And the Winner Is
by wubbzy
Summary: A bet with Drew engulfs May on a journey to win one game of any sport. Realizing just how physically inept she is when it comes to any type of physical activity whatsoever, she decides to ask one of the top athletes at her school for assistance. Will have multiple pairings. Experimental.
1. Danger

**Summary:** A bet with Drew engulfs May on a journey to win one game of any sport. Realizing just how physically inept she is when it comes to any type of physical activity whatsoever, she decides to ask one of the top athletes at her school for assistance. Will have multiple pairings. Experimental.

 _AN:_ I still haven't decided if I want to switch things up and change the end game pairing, or keep it advance like I initially planned. I will have multiple pairings, however. My very first Pokemon multi-chapter fic (finally breaking out of doing one or two shots, haha)! I am about to tread on waters that will either make or break my fanfic career. Place your bets, will I sink or swim in this usually horribly clichéd setting of high school? Either way, I worked really hard on it so I hope you guys enjoy it! This is just an experiment to see what people think.

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 _A Pokemon Fanfic  
_ **Author:** _wubbzy  
_ _Count:_ 4468

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 **And the Winner Is…**

 **.**

Chapter 1  
 _Danger_

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Glances of annoyance and slight twitches of the eyes from her fellow classmates are what May had to endure in her physical education class today. She gulped, her expression doubtful and just a bit self-conscious. She didn't move her head as she stared at the pitcher who was eyeing her with what May can only describe as disgust. Her gaze averted to behind her, where the catcher was looking at her impatiently. It seemed like everyone was eyeing her impatiently, especially as she lamely tapped the bat to the plate, pretending to stretch her arms.

"May, just swing the bat," a girl deadpanned. May sheepishly chuckled to ease the tension, but to no avail. She took a big breath. She was stalling before she made a complete and utter fool out of herself to her female classmates.

"Right." She readied an awkward stance, waiting for the pitcher to throw the ball.

This was not how she liked to spend her times in PE. She preferred sitting on the bench, so much that she had volunteered herself countless times. Today would not be the same as previous classes, however. Her teacher was in a rather nasty mood (rumors of a rather hard breakup she presumed), and she was quite angry that the girl would get an easy A when she did nothing but dress in her PE uniform, yet not break a sweat. No, life couldn't be easy, so she demanded May's participation.

This was why May was led to the batter's box with a bat being shoved her way. Many of the girls on the outfield giggled with a load of confidence that this was going to be an easy win. May felt they took this game a little _too_ seriously.

Why on earth, would winning a dumb game for PE class actually matter?

"May, focus!" her teacher growled. "This is for a grade, you know," she reminded. May sighed, deciding she should at least pretend to put in some effort. She'd get some points and she wouldn't _completely_ fail. Her eyes widened when the ball came her way. She closed her eyes, covering her head and stepping away.

"Strike one!"

"May, keep your eye on the ball!" her teacher lectured.

"Easy for you to say," May grumbled under her breath. She scrunched her face with frustration, annoyed that she could potentially get a serious injury from such a dangerous sport. She could lose an eye! Clearly, her teacher did _not_ understand her predicament.

"May, you can do it!" Dawn shouted as she tried to cheer her best friend on. May looked back as she gave her a thumbs up. Dawn smiled at May's look of concentration until she realized her gaze had quickly lost focus to something in the sky. She soon sweat dropped at the scene.

May Maple was an odd ball. She was ditzy, and wasn't really up-to-date with what was happening. If anyone had anything to say about her, they would say she was living under a rock. Her mind was distorted with day dreams, making her unable to survey her surroundings at all at times. It was easy to tell her head was up in the clouds.

She hadn't even realized she actually hit the ball.

"Run, May! Run!" she heard someone call. She looked behind her, hearing Dawn and her teacher screaming at her to move. She looked over, her surprise evident.

"Oh, I actually hit it?" she asked incredulously, rather proud of her achievement. "Piece of cake!" May laughed, until she heard many of the girls on her team screaming at her to run. May dropped the bat and began running towards first base. She was almost there, too, until she felt something smack her right in the back of the head.

After that, it all faded to black.

.

May blinked, nothing but blurs and a purple spot in her line of vision. May groggily moaned as she felt a sharp pain on the back of her head.

"Are you alright? How many fingers am I holding up?" Dawn asked.

"I think I am, three, and what happened?" she asked.

"You got hit by a soccer ball from the boys' side of the field," Dawn explained. May groaned as she caressed the back of her head, feeling a rather large bump. It was an understatement to say it hurt quite a bit. She was surprised she didn't receive a concussion.

"Now you see why I can _never_ participate in P.E.?" May groaned. She looked up to see her best friend who was giggling.

"It's because you're in the P.E. class for athletes," Dawn explained. May nodded, wondering how on earth she got into that class when she played _no_ sport. In fact, she would like to believe she was more anti-sport, than anything. She couldn't bear to watch any when her dad and little brother are watching soccer, let alone play one herself. In fact, she would consider herself the least inept when it came to sports.

It was annoying because this was the only P.E. class that had a diversity of lower and upper classmen since it was the elite class with all the athletes. She guessed it was because her schedule always got jumbled up. Even when she was a freshmen, they had decided to put her in a class far more advanced than she wanted. It took them three weeks to finally fix it. The only reason why she didn't take this mistake to the counselor was because her best friend was in the same class as her. How was she supposed to leave when it would be the only time they could talk besides lunch time? It was unfortunate for May that her best friend and herself only received one class together. A big disappointment since they held high expectation that they would at least be in three classes like last year.

May sighed, realizing it would never go her way.

"That's not the point. Have you noticed that I'm just not good at sports? They are _so_ boring," May dramatized. Dawn giggled at her friend who acted like a drama queen and made a big deal out of nothing.

"Stupid soccer ball," May complained as she rubbed the back of her head. "Stupid boys. They should really watch where they kick." Dawn shrugged.

"At least you got out of P.E. early," she mentioned, making May brightened.

"Is class over?" she asked. When Dawn nodded, May's face instantly fell with panic. "That means we're missing lunch!"

.

"Ah, my favorite time of the day: lunch!" May exclaimed as her stomach growled. Dawn sighed in exhaustion; May would never change. "Today's my favorite: pizza and tator tots!" May reminded her.

"Wow, you sure forgot about that hit to your head," Dawn observed with a smirk.

"Of course I didn't. I'm still mad, it's just subsided for the mean time," she explained as she grabbed a carton of milk and placed it on her tray. "I need my nutrition to get this healed, you know." May laughed at Dawn's unconvinced expression.

"Anyways, I wanted to talk to you about something," Dawn presumed as the two walked to their usual table. The two were the only ones at the table. At the very least, before an uninvited guest greeted them. There, May's archenemy (at least that's what she called him since middle school), Drew LaRousse. Dawn frowned, wondering why they were never on good terms now. However, May was always very vague about Drew, instead resorting to name calling.

Drew came up to them with his hands crossed over his chest and a large smirk on his face. He only uncrossed his arms to move his green hair out of his eyes.

"I heard about what happened today." May immediately became exasperated by the boy in front of her, her fist clenching in anger.

"What, came to make fun of me?" May asked in annoyance. He shrugged.

"I just came to see if you're hurt is all. Don't want to lose any more of your brain cells." Drew smirked at the scowl on her face.

"Tell me why you're really here," she demanded as she sat back in her seat and crossed her arms. She eyed the boy, knowing it couldn't be anything good. Drew brought his hands to a shrug.

"Believe it or not, I'm just trying to help. I just thought you might want to know who hit you," Drew told her with a bit of smugness to his demeanor (a bit more than usual, May noted). May's anger subsided as she asked, "Who, you?" May assumed as she glared. Drew laughed, shaking his head.

"As if I'd ever _not_ have control of the ball," Drew defended, a bit offended. May rolled her eyes. "It was that Ketchum kid, actually." Dawn gasped when she saw May fume.

"Oh really? Watch when I see him! He better apologize!" May said as she raised invisible sleeves and clenched her fist. Although Dawn frowned, seeing as May was taking this way too personally.

"It was an accident, you know," Dawn reminded, thinking she should really be thanking him for excusing her out of P.E.

"Either way, I deserve an apology!" May said as she stood up. She then stopped herself, staring into space. "Ugh, who's Ketchum again?" May asked as she rubbed the back of her head sheepishly. Drew sighed with a small chuckle while Dawn's eyes widened in sheer shock.

"You don't know who he is? He's probably one of the best athletes on the basketball, football, baseball, track, _and_ soccer team," Dawn told her in astonishment while Drew merely chuckled in understanding.

"It's not a shocker. Obviously she wouldn't know the top athletes at this school. She's so ignorant when it comes to things like this. May's such a noob."

"Am not!" May countered as she glared at him. "I'm tired of you always making fun of me! I'm way better than you!" Drew eyed her.

"Is that so?"

"Of course! I can do anything better than you!" May crossed her arms. Drew smirked.

"Are you sure about that?" he wondered self-righteously.

"Sure I'm sure! In fact, I bet I could at least beat you at something… anything!" May exclaimed just as haughtily.

"Hah, I bet you can't even win a single game of any sport that's in this school," Drew said as he crossed his arms with a certain authority that could intimidate just about anyone. However, May's demeanor hadn't faltered. In fact, she smirked with nothing but confidence.

"You're on. If I win, then you have to admit I'm better than you in every way," May declared. Drew sighed.

"I have nothing to lose. I'm completely confident that you'll lose." May smirked.

"…in a dress, in front of the whole school," she finished. Drew paused, glaring at the girl. She grinned. "What, are you scared now?" Drew turned his head away, flicking his hair away from his eyes.

"Of course not. But if I win, which I will, you will… come to school in clothes of my choosing, and you'll stand up on the table and repeatedly sing that I am better than you in every way, to the tune of 'I'm a Little Tea Pot." May gulped, but never avoided eye contact, no matter how much his eyes pierced right through her.

"Now, are you sure you want to do this? I don't want to embarrass you, you can back out you know," he told her. May glared.

"As if I'd back out. It's a deal," she exclaimed, bringing her hand out to shake on it. The two shook hands, and she glared his way, trying to give him her meanest of glowers. Drew swiftly wiped his hair away from his eyes once more before he walked away. May sighed, sitting back down to continue eating. Dawn just sat there, gawking at the events that transpired.

"What were you _thinking_?" Dawn gasped. May nonchalantly shrugged, taking a bite into her pepperoni pizza.

"I'm thinking I finally want Drew to admit I'm better than him! He's always ahead of me, and I hate that! It's about time that he realizes that I may not be the most observant, but I am just a cool a person as he is!"

"I get why you might want to show Drew up – actually, not really, but that's besides the point – but you're going to accomplish it like this?"

"What do you mean?"

"May, you said you'd be able to win a game of any sport," Dawn reminded her. She shrugged once again.

"How hard can that be? I'll just find an easy sport and just wing it. It can't be that hard. I mean, there's golf, ping-pong, foursquare... Easy." May grinned as she took a sip of milk. Dawn frowned in concern.

"I hope you know what you are doing."

"Well, I can't turn back time anyways. Nothing left but to move forward!"

"Well, you know you need to make a team then." Dawn trailed off.

"Really?" Dawn nodded.

"Yup. Which means you should try out or join some club or something," Dawn suggested. May grinned.

"Yeah, I'll definitely do that! See? This is going to be a piece of cake," May said as she took another bite of her pizza. Dawn sighed, hoping her friend wouldn't humiliate herself – _again._

And so, tryouts began.

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 **Golf…**

"Don't I look cute?" May posed as she showed her friend her white golfing uniform. Dawn sighed, face palming.

"I think you should be worried about making the golf team than how cute you look, May. Although, gotta admit, those shorts are fabulous. I need to borrow them sometime." May wasn't one to pay attention when someone reprimanded her, so she had been pretending to concentrate on the ball.

May grinned, swinging the golf club.

She swung the club, and soon wondered where the golf ball went.

"Woah, I must of hit it so far it went out to the atmosphere!" Dawn sighed at her cluelessness.

"Ugh, May?" She pointed to the floor to show her the untouched golf ball.

"Huh? But I hit it! I'm sure of it! This game must be rigged or something!" May complained as she stared at the golf ball. "Fine, I'm not one to give up! I'll just try again. No need to worry, right Dawn?" She winked when she said Dawn's usual catch phrase, and Dawn shook her head, sighing at her friend's antics.

"Sure…" she trailed off, wishing she'd just swing the ball. May readied herself, getting realigned with the ball. She swung the stick, and then quickly looked down to see if she hit the ball.

"This time I must have…" her eyes widened when she saw the ball up in the air above her, hurling down.

She definitely hit it alright...

And this was how May earned a second bump on her head.

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 **Tennis…**

 _"This_ will be a piece of cake!" May said aloud as she stared down the machine that was about to throw tennis balls. She was sure her forehead was still throbbing from the pain of the golf ball, however, she wasn't about to give up on finding her forte. She wondered how on earth she didn't get amnesia from such a traumatic hit to the forehead, but she quickly dismissed it, moving on to her next challenge.

"Ready?" Dawn asked. May nodded, readying her stance and her tennis racket. Dawn turned on the machine, and it began to shoot out tennis balls.

"Whoa, why is it trying to hit me?"

"You're supposed to hit the ball, May!" Dawn reminded. "Don't be afraid of the ball, attack it before it attacks you!" she advised. However, her words were in vain for she was sure May was too busy screaming to hear her.

Unfortunately, the balls attacked her before she had a chance to attack them.

"I don't think tennis is your thing." Dawn sweat-dropped.

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 **Volleyball…**

Volley ball…. No, let's not talk about volleyball.

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 **A few failed attempts later…**

May flopped down to the pavement, incredibly exhausted.

"Nothing! I'm not good at any sport! What am I going to do?" she cried to the skies. Dawn stared down at the girl with a frown.

"Do you want to try cheerleading?"

"Cheerleading? That's not a sport." Dawn shrugged.

"Maybe not to you. But I just thought you'd want to go with me to cheer you up." May sat up and stared at the girl.

"You're trying out?" May questioned. Dawn grinned.

"Yup!" Dawn smiled excitedly. "I was hoping you'd be there wishing me luck. Hey, maybe it will give you the confidence you need."

"Alright!" May grinned.

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Cerulean eyes shined at the prospect of her best friend began her routine.

"So cool! Gymnastics really made her a shoe in to win," May commented as she stared at her friend audition. With the way the team had been looking at her throughout her performance, May could tell that she was already in.

Dawn had ended with a back flip, her arms stretched out into the air as she posed in her stance. May's eyes widened as that back flip turned to the splits, as though it was nothing. The music ceased, and the next thing she heard was clapping and cheering.

"Wow, we could use a girl like you on the team. Well, thank you for auditioning, we'll be sure to tell you the results on Monday, we just have to see a few more of the other auditions," the team captain told her. Dawn nodded, when she felt another one of the team's cheerleaders whisper in her ear, "but from what we've seen, you're definitely in." Dawn grinned even more, excited at the thought. She thanked the team as she headed towards the bleachers where she instantly embraced May as the two squealed.

"Wow, you were amazing!" May complimented.

"Thanks! It took me a while to think of that routine, but it paid off." They walked towards the girl's locker rooms as Dawn started telling her, "You know, why don't you ask a really good athlete to help you out?" May tilted her head at the possibility. "I mean, I don't know if they'll agree to it, but it's worth a shot!"

"You're a genius!" May shouted in realization.

"There are three amazing athletes you could ask that I heard lead our football and basketball team to victory last year: Paul Veil, Gary Oak, and Ash Ketchum. Get this though: they were only sophomores when they became the leaders," Dawn announced, stars in her eyes at the thought of the three athletes. May's eyebrows rose.

"Is that good?"

"Good? It's phenomenal! That's unheard of to be a sophomore and accomplishing _that_! People usually can't even make it into the Varsity team as a sophomore. However, they were so good, they made it as freshmen – or so I've heard." May scratched her head.

"If what you say is true and they're really that good, then maybe I should ask one of them for help, don't you think?" May suggested, and Dawn deadpanned.

"That's what I just said…" she muttered as May hugged Dawn tightly and ran off towards her locker. Dawn sighed, wondering if she should have told her that there were actually _four_ great athletes, and Drew was one of them. She frowned, knowing May wouldn't want to hear that. Not only would May not ask for his help even if he was the last person on earth, she was also sure it would be a real downer. May would rather run 100 laps than ask Drew for help. Deciding against mentioning it, Dawn shrugged, heading for the showers.

.

May was in complete thought, wondering how she would go about her next plan of action. She had never heard of either of the three except for Ash Ketchum just recently. Though, he was the one who hit her with the soccer ball. She was still a bit upset that he _still_ hadn't apologized. She never even heard of Paul Veil and Gary Oak till Dawn mentioned their names, too. Although… she was sure she heard girls say their names when in the locker rooms. Now that she thought about it… yeah, Dawn was fawning over them all freshmen year.

"Well, all I know is I should at least know who these people are before I ask for help." She realized it might have been a good idea to actually get a picture so she wouldn't have to be shouting out their names in the cafeteria. "Maybe Dawn can show me who they are since she practically knows everything about them. Well, more than I do at least." As May walked down the hall, she happened to notice the hall of fame that held the trophies and photos of the star athletes.

"Well, that certainly is convenient." May stared at the names around the biggest trophy she had ever seen. It was so entrancing, the way it practically illuminated the empty hallway. She read the names: Ash Ketchum, Drew LaRousse, Gary Oak, and Paul Veil. She paused, taking a double take. _Drew?_ May grimaced at the name. "What's _he_ doing in there?" May's arms crossed in exasperation. She briskly turned, furious, not wanting to look at the photos of the four athletes, when she bumped into someone.

"Oww," May groaned. Great, if her day couldn't get any worse…

"Sorry about that." A hand tersely came to her view as the only thing she could think of was how irritated and inane this day had been for her. It was only when she finally noticed the hand in front of her that she finally got out of her stupor and took it.

"Thanks. And it's okay." May looked at the boy, and her eyes widened. The raven haired boy smiled as he waved goodbye to the girl in a stupor. He was heading towards his locker it looked like. She turned and looked at the photo behind the glass, then stared at the back of the boy who was just leaving. "No freaking way," May whispered to herself as anger began to settle in. "Hey, you wait right there, Mister!" May called as she ran to catch up to the boy. Said boy turned around with a quirked up eyebrow in wonder.

"Huh?" Ash had already made it to his locker by the time May finally caught up. She was panting, out of breath. _"How can he walk so fast? I really should stop being so lazy,"_ she thought.

"Why hello there, Mr. Ketchum." Ash turned in a bit of surprise at the irritated voice behind him.

"Urm, hey. Can I help you with something?" he asked as he started to grab his books from his locker.

"Oh, just my swollen head," she said in annoyance as she crossed her arms and glared at the boy. He titled his head in confusion. She gritted her teeth. "Well, if I have to spell it out for you: you totally hit me in the head with a soccer ball today!" she confessed. "I'd really like an apology." She crossed her arms as she turned away from him.

"Oh, really? I didn't even know I hit someone, I'm sorry!" he explained to her, sincerely sorry. May smirked, happy with the response. This was her chance.

"Thank you." He nodded, returning back to his locker. "But I really need something in return," she told him, her smirk growing to both sides of her face. Ash sensed something was up, so he gulped. He soon glared at the girl, wondering what her deal was.

"It was just an accident, I don't know why you're getting all defensive about it," he said, placing his hands in front of him in defense.

"Well, I was wondering if you could do me a huge favor," she began, placing her hands on her hips. He predicted it would either be something bad or weird. Ever since he was recognized as a top athlete and kind of popular, there were a lot of girls talking to him now, which was kind of weird now that he thought about it. They talked about odd things, those girls. Never once did they talk about sports, the reason why he was so popular, but he had shrugged it off, coming to the simple conclusion that girls were weird. However, as he stared into this girl's azure orbs, he couldn't help but think this girl was a different kind of weird…

She was _strange._

"It's just. Y-you're a really good basketball player, aren't you?" she asked, flustered. She twiddled her fingers together in embarrassment. He nodded.

"Yeah, I'm kind of the best, if I do say so myself." May's eyebrow twitched a bit. He was certainly cocky about it. So much for modesty…

"Well, I kind of need your help then. I-I really want to make it on the girl's basketball team!" confessed May. "Can you please teach me everything you know about basketball?"

"Huh?" He frowned. "That seems like it would take a lot of time. Time that I won't have with practice starting up soon and-"

"Please?" she interrupted, getting on her knees and begging. "Is there any way you could at least give me some tips and pointers?" she asked hopefully. He thought about it, and then smiled.

"Urm, I guess I can give you a few tips and pointers." He shrugged, although a bit reluctant to agree, since he knew there would be consequences. He wondered how he would make the time for this when he had other responsibilities, although if it were only to give a few pointers for her, it couldn't consume so much time, right? May's face lit up. She instantly embraced him, feeling giddy and inwardly smirking at the prospect of finally showing up Drew.

"Thank you _so_ much! Oh, you don't know how much this means to me! You are the best!" she yelled. She happily let go, beginning to skip her way through the halls. Ash scratched the back of his neck and fixed his hat, realizing his hair was now wilder than before May's attack. It was such a strange encounter with an even stranger girl. She definitely made some first impression…

The only adjective he could think of was weird. She was also incredibly odd; it kind of freaked him out a bit. He decided to shrug it off, instead grabbing the rest of his books and closing his locker.

Ash's eyes widened, pondering a bit. He hadn't even gotten her name. He sighed, figuring she had already left the building.

He shrugged, walking out the school to head home.

If she really wanted his help, she'd find him again… eventually.

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 _AN:_ I am planning to add multiple pairings, maybe a bit of everything, we will see. At the same time, romance is not the main priority. It will just be subplot to the main idea. It's not really about pairings, so I will see if I can add a few scenes to certain pairings. If there's a particular one you might want to see, speak now or forever hold your peace.


	2. Evaluation

_AN:_ Thank you so much for all the feedback! :D I was honestly shocked that so many would be interested in this fic I'm testing out! Bit of a warning, the character's personalities are pretty exaggerated on purpose (genre is humor for a reason). xD I would also like to apologize in advance, because I haven't edited this the way I normally would. I am super tired, but wanted to post this. Enjoy!

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 _Count:_ 4100

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Chapter 2:  
 _Evaluation_

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Ash turned to eye the boy next to him. Said boy next to him, Gary Oak, eyed Ash right back, smirking. Gary was so confident he knew he would win.

To any of the track and field athletes watching the two, it was just a practice 100-meter dash.

To Ash and Gary, it was much more than that.

They have been rivals since they were kids. They always competed against each other, and today was no difference.

Practice or not, both Ash and Gary took this race very seriously.

"You know I will win, right?" Gary spoke smugly.

"You wish," Ash countered, staring straight at the finish line, knowing where he was going to be very soon, in a matter of seconds. Their PE teacher/ coach brought the flag up.

"On your mark," their coach began. Ash tensed up a bit, his muscles ready to spasm into a sprint with how much anticipation he was holding.

"Get set." Gary clenched his jaw, in wait for when he can and _will_ win. Ash felt his heart racing, adrenaline beginning to run through him as he prepared. There was a pause. To Ash, it felt like a lifetime passed, and he gave this moment complete focus.

"Go!" the coach yelled. Finally, the coach brought the flag down, and they were off, sprinting away. Ash didn't dare look next to him, to see where Gary was – if he's ahead or behind. He couldn't. Ash didn't think of anything but the finish line, in complete concentration and focus. It was necessary, if he wanted to win.

When Ash finished, he looked towards the assistant at the finish line. Both Gary and Ash did, wondering who won.

"Tie," the assistant announced, looking at is stopwatch. He smiled. "The best time both of you two ever had."

"How?" Gary panted, kneeling.

"What can I say? Both of you are my best and on par with each other. Good going. Maybe a little competition will help," their coach said, excited at the prospect. This was their absolute best time. Ash was panting, proud that he made his best time, but a bit annoyed… _extremely_ annoyed. He definitely did not intend on showing his annoyance. He instead decided to smile with accomplishment, staring at Gary rather haughtily.

He had reason to give Gary a smug smile. There was a time where he would lose to Gary in such a horrible defeat. As a child, Gary would laugh in his face at how slow Ash was, or how bad he was at different sports as opposed to him. But now, the tables have turned.

He definitely progressed since that time in his life.

"Just a stroke of luck, Ashy-boy," Gary panted out, smiling just as smugly as well.

Even though he has progressed, Gary still treated him like that same kid that lost to him. This is what frustrated him to no end. Hence, why he wanted to utterly crush Gary Oak, even in little practice races like this one.

Because a tie wasn't good enough for Gary.

And it wasn't good enough for Ash, for that matter.

But he was getting there. And for that, Ash boasted confidence after their tie.

"We'll see about that next time," Ash said as he made his way back to the locker room. "Luck has nothing to do with tying you all the time. Or maybe you're just not as good as you used to be." Ash shrugged, but soon made his way to the locker room. Gary glared, annoyed that Ash was getting the better of him.

The guys gave Ash a high five as he did so, with Ash grabbing his water bottle and gulping it down. His towel hung over his shoulders as he decided to hit the showers before lunch.

During and after his shower, his mind wandered to later today, and how practice will most likely be brutal today.

He recalled that he would meet May again, too.

She found him like he assumed, this time with her friend, Dawn. That encounter was a little more normal than when he originally met May. However, his brain was scrambling to remember Dawn. She had told him that they met before, but he couldn't, for the life of him, recall. She gave him a big smile, waving him off and saying how he didn't need to worry about it, but worry he did.

She did seem extremely familiar.

"This is going to eat at me for the longest time," he said aloud as he dried his hair.

Either way, during their last encounter, both Ash and May agreed that they would meet today for some tips and help with basketball.

Their friends usually would hang out after practice, but today would be different. He had to think of an excuse, so he could keep it a secret, like May asked

.

"Oh! By the way-" May had called to him. Ash turned. "Can we keep this a secret? Please?" Ash's eyebrow rose, confused.

"Why?" he asked.

"It's, kind of embarrassing. I don't want people to make fun of me," she lied. In reality, she didn't want Drew to find out, and she knew that Ash and Drew talked every day. She didn't want him knowing she was having extra assistance to cream him.

"Sure, I guess." Ash shrugged nonchalantly, not thinking much of it. "Well, I'll see you tomorrow after school then!" Ash called, waving goodbye. Both May and Dawn waved back, May sheepishly laughing as she waved goodbye.

.

Ash nodded to himself as he got dressed, listing all the things he had to do in his head so he wouldn't forget.

The rest of the day was rather normal.

.

At lunch, Ash grabbed his food and sat at his usual table with Brock, Misty, Gary, Drew, and Serena. All, except for an always late Drew, were at the table chatting up a storm. He quickly greeted them before devouring his food.

"Hey, so we're all going to hang out after practice, right?" Misty wondered.

"Yes please, I am going to need a long break after racing," Serena said, already exhausted.

"Why don't you just tell your mom you don't want to race anymore?" Brock wondered with concern. Serena tended to put herself in predicaments that could easily be avoided with communication. Serena sighed, explaining for the hundredth time.

"I told you already, I can't disappoint her like that. She would be devastated. Plus, scholarships for college, you know…" Serena said miserably, her chin resting on her palm with a dejected expression on her face.

Gary smirked.

"Hey, if you're just worried about disappointing your mom, then why don't you just say you're going to practice, but do something else instead, something you actually like," Gary suggested. Serena gasped.

"No, I can't do that… can I?" she wondered. "I can't just lie like that."

Gary grinned, "Do something spontaneous for once, stop listening to mommy all the time… like Ashy-boy over here." Serena stood, annoyed at his remark.

"Hey, stop being such a jerk! That's not true!" Serena attempted to defend. She looked over to Ash, to see Ash was not even paying attention.

"Earth to Ash!" Misty called, waving her hand in front of him. That didn't seem to do much.

It took him a full minute to realize Misty was calling him.

Finally, Ash shook from his stupor.

"What are you staring at?" Brock wondered. He looked over at the direction Ash was, to see Drew talking to two girls. He chuckled, "Oh, that." Misty sighed.

"Drew is just being his usual heckling self. He always talks to those two girls. Don't know why," Misty explained, shrugging.

"He does?" This was news to him.

"Yeah, I think they're sophomores." Misty giggled, "He's probably into one of them."

"Or both," Gary chimed in, nodding in approval to Drew. Both Serena and Misty gave him a disgusted expression. Brock gave off a small chortle at his comment.

"Hey, who are those girls?" Ash asked, hoping they would know. If Drew always talked to them, he wondered why he never saw them at lunch. Ash and Drew were always around each other – usually. He assumed it was because their table was at the very corner, kind of hidden away from everyone else. Although, to be fair, he never really looked to see where Drew was, nor did he notice many people during lunch, caring mostly about eating than anything else.

Ash continued to watch as Drew walked back to their usual table.

"Yo," Drew waved.

"Hey, how do you know those two girls?" Ash wondered. Drew pfft'd, shaking his head and eyeing him suspiciously.

"Wouldn't you like to know…" he sneered. When he sat down, he casually added, "they're no one important," he said, and Ash glared, annoyed that Drew could be so frustrating and be around the bush. But that was Drew's personality. There was a time, when they first met, that Drew buried this side of him. However, that was when Drew was only a freshmen and no one knew what a great athlete he was. That soon passed a few days after Ash invited Drew to sit with them. Sometimes, like right now, he wish it hadn't.

"Whatever," Ash said under his breath.

"Drew, are you going to hang out with us after your practice?" Brock asked. Drew shrugged, saying he had nothing better to do. It wasn't till then that Ash remembered he had to tell them he couldn't hang out today.

"I won't be able to make it," Ash said, and Serena's face fell.

"Why?" she asked.

"I have other obligations, you know," was all Ash said. They all seemed to understand.

"Oh… okay," was all Serena said before acting as though it didn't affect her. She smiled, "Well, maybe next time?"

"Yeah, definitely," he reassured. He at first was worried that they would question him, but glad they didn't. He always had other things to do, whether it be helping his mom or finishing homework. It was then that Ash decided to not concern himself with predicaments that were for later today. He'd rather spend his lunch period stuffing as much food in his mouth as possible.

.

May sighed, angered as she slammed her palms on the table. She leered at Drew's back as he walked away to his usual table.

"Oh, that Drew! I swear, that guy is out to get me!"

"Are you sure it's not the other way around?" Dawn laughed, while May glared.

"He's the one that comes to our table," May argued back. She crossed her arms, smashing her butt to the chair and pouting very child-like.

"Good point," Dawn agreed. May subsided her anger for Drew, and smiled, looking at Dawn expectantly.

"Anyways, why didn't you tell me you knew Ash already? When? How?" May interrogated, eyeing her suspiciously. Dawn backed a bit, her face heating.

"It's nothing, it's nothing! It was a long time ago, anyways, and he doesn't even remember, so there's no need to worry!" Dawn shrugged nonchalantly as though it was nothing. However, May saw through her feigning indifference.

"Wait… Ash was the one you had a crush on? I bet I'm right!" May gasped, putting two and two together. Dawn used her hand to shush May's lips.

"Can you be any louder?" Dawn sneered.

"You know I can…" Dawn rolled her eyes at her friend's words. She sighed, letting go of her as she sat back down.

"The short answer: yes, but let me be clear, I had a crush on _all_ the athletes at one point or another," Dawn explained. She shrugged, "I'm a sucker for the athletic types, what can I say?"

"All… Wait… does that mean…so, Drew too?" she wondered, a bit concerned with a hint of disgust. Dawn scratched her cheek, in thought.

"I mean, I guess, technically, you could say so. But only for a minute, I swear!"

"I feel so betrayed…" Dawn waved her off.

"Stop being so dramatic. It means nothing, just like my crushes on any of them meant _nothing_ ," Dawn reassured, laughing awkwardly. May shrugged. "Anyways, yes, Ash was the one I had a crush on, but he's so dense, he doesn't even care about girls right now. He's too worried about sports." Dawn shrugged. "I moved on, obviously." May nodded in understanding.

"He does seem dense. And I mean _really_ dense," May noticed.

"Yeah, I don't know if that's ever going to change," Dawn laughed. "But, all of the athletes are really cool from afar, but apparently have extremely big flaws. There are even rumors that they may all be gay for each other – except Gary. But I don't believe them to be honest," Dawn giggled at the thought.

"Ash, as I said earlier, is extremely dense. Drew-"

"is a narcissistic butt," May interrupted. Dawn laughed.

"Well, that's not what I was going to say, but sure. And Paul, is so mysterious, but he may be _too_ mysterious. He is an extreme loner. None of those three ever care for their fangirls, really. The only one who's actually held a girlfriend is Gary, but I mean – he goes a little too far at times from what I heard. But, like I said, they're all just rumors. I heard the girls that were lucky enough to score dates with them were in for… Well, let's just say they never ended well," Dawn said.

"Weird…" May commented. Dawn nodded.

"Yeah, but that doesn't stop almost _every_ girl from fawning over them. But, like I said, just rumors. Who knows if that's accurate."

"Well, I guess that doesn't really matter much to me," May admitted, ready to chow down and devour her food.

"Yeah. Honestly, it's just an infatuation from afar with all of them. Like how someone admires their favorite athlete on their favorite sports team. Well, it's exactly like that. That's all there is to it." May nodded in understanding.

.

May waited and waited... and waited and waited. She crossed her arms and impatiently tapped on the pavement. She was extremely annoyed that she had to wait so long.

"He said to meet by the basketball courts, and he's not even here! What's taking him so long?" May wondered, annoyed.

She waited, and still, she waited. She didn't know why she waited so long, but she wanted to believe that Ash would keep his word. He didn't seem like a liar.

"He stood me up… he really did. He's such a liar." May crossed her arms, blowing her bangs out of her face.

After an hour of waiting, she finally decided to head home. She grabbed her things and stuffed them into her bag, getting ready to leave. During this process, she heard footsteps.

"Hey! Okay, are you ready to start?" Ash looked confused, wondering why she was packing her bags.

"Start? You're late! I was just about to head home because you didn't keep your word!" Ash looked extremely confused at this.

"No, I'm not. I had practice. I told you," Ash began. May blinked, thinking back.

"No, you just said afterschool, so I waited afterschool for almost an hour!"

"I'm pretty sure I mentioned practice started today." May paused, thinking back.

He did mention something about practice.

"But I thought you meant our practice."

"No, I meant official practice with the team," Ash corrected. She began to sheepishly chuckle as she rubbed the back of her neck.

"Okay, okay, well, then let's just drop all that. I was just an hour early then. But anyways, what should I do first to get in tip top condition to join the girls' basketball team?" she asked, enthusiasm in her voice and fire in her eyes. Ash stopped to think for a moment.

"Well, I have to see how you do, where you stand."

"Where…I… stand?" she asked perplexed. Ash nodded.

"Yeah, I need to figure out how good you are and how much you know already before I can help you." May laughed, waving her hands.

"I don't think that is necessary. I know nothing about the sport! I am a complete and utter beginner!"

"Really?" Ash tilted his head. "Then why do you want to join so much? Do you even like basketball?" he wondered, a big frown evident.

"Well, let's just say I have a determination right now that will only be solved through learning basketball." Ash quirked an eyebrow, even more confused. He sighed, deciding to drop it, on the count of May being incredibly confusing since he first met her.

"Well, let's just get started, shall we?" May cheered, excited for what was to come.

Ash began to bounce the ball on the basketball court, dribbling between his legs. May was amazed by how well he handled the ball. He soon brought it to his chest.

"Catch," wasall Ash said before he hurled the ball her way. She yelped, attempting to be cool and grab the ball without looking too foolish. "To evaluate how you do, the first thing I want to see is your dribbling abilities. So to start off, just dribble up and down the court," he explained as he began adding cones to make a small obstacle course.

He soon realized, adding cones was not necessary.

May didn't need them.

Ash saw May handle the ball as she staggered down the court. He came to realize she was far too gauche, concluding she's never picked up a basketball in her life. She would continuously knock the cones either with the ball or her feet. Maybe it was a measure of hyperbole, but it didn't change the fact she wasn't exactly enamored for the sport. Actually, her incoherent grumbles as she vilified the sport told him she must dislike it fervently. He crossed his arms with apathy. He could not help someone if they didn't like the sport.

"You're not taking this seriously. Sorry, but I can't help someone who's only wanting to goof off and doesn't actually want to improve," he harshly told her. She fell on her knees at his words, cringing at his burning glare. She was not used to this. She didn't expect to disappoint him at all. She whimpered, her eyes watering, knowing he was her only hope in beating Drew. She crawled over, begging, as pathetic as that felt.

"Please, you have to help me! I heard you're the best athlete at our school! Please, I want to be really good!" she all but shouted, clutching on his shoe.

"E-eh, May, do you think you can stop tugging on my leg?" he asked.

"I'm usually not one to beg, but please! You are the only one that can help me!" May confessed. "I'd do anything!" Ash crossed his arms, in thought.

"Well, you'll have to do all my chores then," Ash said.

"Deal! I'll do that!"

"Seriously?" Ash eyed her, confused. He didn't understand why she wanted to join the basketball team so bad.

"Yes! I meant it when I said I'll do anything. My reasons, are… private, but, just know that I have never been more dedicated or devoted to anything in my life!"

"I can believe that," Ash mumbled, and May shot him a glare. Ash sighed, realizing this might be a lot more work than he initially got himself into.

"I have to get on the basketball team! Please, Ash, you have to help me! I'll do all your chores, your homework, you name it!" He looked down and stared at her pleading eyes, sighing. This was definitely going to take more time. It wasn't going to just be giving May some tips on the sport.

"By the way, I was just kidding about doing my chores. I don't get chores. I just have to make sure my room is clean, and I'm not going to make you clean that," Ash reassured. He didn't really have chores with his mom around. Plus, he was an only child and was mostly out of the house, which made it easier to keep clean (Delia would beg to differ). None the less, his mother understood he had a lot on his plate. Ash trying to maintain his grades was hard enough: he had to study more than the other students just to get by with C's, good enough to play sports. Out of all four boys, he lacked in book smarts the most. He never understood how it came easier to Drew and Paul.

He got out of his stupor to realize May was _still_ latched onto his leg. Oh boy.

"Okay, if I'm going to help you, then I need you to promise me something, okay?"

May's neck could have snapped with how frantic her head was moving up and down.

"Of course, of course, anything anything!"

"First, stop tugging at my leg." When he said that, she immediately let go. "Second, you have to give it your all, and always try your best. Take this seriously! And no distractions! If you want to be good, it's going to take a lot of hard work, and you're going to have to be willing to put in that time and a lot of effort… I mean _a lot_!" he stated, recalling her dribbling and shooting skills.

"Yes, yes of course! Anything!" Ash nodded. "Okay, so, what we're going to do, is start by running laps! It will help raise your stamina. I can tell you don't work out much."

"L-laps?" May asked, fear- stricken. Ash nodded.

"Yes, laps. You said you were willing to do anything."

"I-I am… just… laps kind of, aren't my thing," May said. To Ash eyeing her, she raised her hands, waving him off, "But I am willing to do it! Because I am that dedicated! You want me to run a lap? Darn right I will! I'll even run two!"

"I was thinking, more like five, since you are just starting," Ash said, and May's face fell, horrified. She gulped.

"Oh… O-okay. Here I go then," May said awkwardly. Beginning with a slow trot. She kept looking back to Ash, hoping he'd say he was just kidding and 5 would be too much…

…but no such luck.

"You're not going to finish by sundown if you keep looking back and running so slowly!" Ash called.

"Right! Right," May whispered the last right, in the back of her mind, wondering if all of this was a mistake. She shook out of her stupor, realizing she needed to be determined.

"This is all part of the deal. I have to do this! I already promised Ash I will give it my all, so that's what I have to do!" May talked to herself, staring up at the stars as she gained motivation to see this through.

.

"Okay, may, it's getting late… you only did 2 and a half laps," Ash analyzed, frowning.

"Ash! Ash, I am trying my best, I am going to keep going! I will not stop until I finish 5 laps!" May called in between heaves. "You- you have to believe me!"

Ash motioned for her to stop, while May collapsed to the floor. Ash squatted down, offering her a towel and a bottle of water. He smiled.

"I believe you, I believe you. Okay, we'll pick this up tomorrow. Next time you will do those 5 laps, okay? Not only that, but we're going to start doing _real_ drills for basketball… before you even touch a basketball," he warned. "You need to increase your speed and agility too. But for the first day, this is fine. I'll see you tomorrow."

"Alright, can't wait! Bye!" May said happily, waving goodbye.

Once she was sure he left, she collapsed again, heaving for more air.

"He's is going to kill me!" she breathed out, wondering what exactly she got herself into. "He's crazy," she mumbled.

Whatever it was, she was going to stick to it till the end, whether or not Ash really will be the death of her.

As Ash walked off, wondering what he got himself into. He wondered if this would be possible to get her on the basketball team. Either way, he was going to have to teach her as much as he could.

He couldn't help but wonder why a girl would work so hard to get on the basketball team when she has no knowledge of the sport. However, Ash soon shrugged his thoughts off, knowing that there was only one explanation possible.

Ash mumbled, "She's crazy."

And so, practice to do the impossible began.

.

 _AN:_ And that is the second chapter! You know, you guys really changed/helped the direction of where the story was going! xD if I am being honest, pearlshipping wasn't even on my radar. I was planning to add advance, contest, and a whole bunch of other ships, but pearl wasn't one of them. xD if you want to continue to contribute to the pairings, please keep letting me know! Also, if you guys spotted any errors, please let me know!

Also, if there is a particular endgame pair you want, please persuade me on whichever ship your heart desires. I am legitimately debating what pair should be the end game (I am extremely conflicted right now), so your input helps! Thanks again and I hope you guys enjoyed this chapter and hope to see you next chapter!


	3. Board

_AN:_ Welp, thanks you guys! I am happy with all the feedback! Also, I know a lot of people want pairings (as I can see from all the reviews asking for them haha). I heard all of you loud and clear, and I plan to take all your suggestions into consideration! Like I said in the summary, it will have multiple pairings (a lot of them might seem subtle at first), so I plan to find a way to weave all of your suggestions together. What I'm thinking is hard to explain, but just know I heard all of you and hope to do something with everyone's suggestions! But like I said, I want this to be humor and friendship and sports first, so when I do add different pairings, like I said, it'll be subtle (sometimes not so much). Also, I will say if there is an end game pairing, it's narrowed down between Pearl, Advance, Contest, or Amour. However, I am going to add a lot of funny pairings stuff in between that's not with these, just to be warned. I don't know if any of this makes sense to be honest haha. But anyways, I hope you guys enjoy!

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 _Count:_ 3048

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Chapter 3:  
 _Board_

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May was extremely bored.

Like, _really_ bored.

She frowned.

"What am I supposed to do while Ash is at practice? Just wait at school doing nothing?" May wondered as she lay splayed on the grass. May turned to her side to eye Dawn curiously.

"Dawn, can you stay with me afterschool until Ash gets there for our practice?" May asked. Dawn frowned, shaking her head no.

"Sorry, I can't. Actually, I guess now is as good a time as any to give you the news: I made the cheerleading team!" Dawn exclaimed.

"Congratulations! I knew you could do it!" May congratulated, hugging Dawn.

"So that means I won't be able to stay with you. I actually start cheerleading practice tomorrow!" May nodded.

"That means we can hang out for today, right?"

"Well, I actually have to go to the nurse's office for a check up to make sure I'm good to go for cheerleading," Dawn explained. May sighed.

"Well, that's good that you made the team and you're getting everything sorted out! But that's a bummer you won't be able to hang out with me. What am I supposed to do till then?" May asked, a bit dejected.

"I mean… you could practice yourself. Or find a different afterschool activity," Dawn suggested, shrugging. May's face brightened at the idea.

"That's a great idea! Quest to find another afterschool activity begins… now!" She announced, getting up and running back to the school.

"May… wait up!" Dawn called, wondering why she decided to run now of all times.

.

 **Art Club**

May sulked, looking at her canvas that was rather bland. All she decided to paint was a stick figure woman a mediocre sun, and a single green line she called grass.

A painter, May was not.

"Out of all the clubs I find, why one that I _know_ I'm not good at?" May asked herself. Countless projects and bad elementary (and middle school) drawings said enough about her skills in the arts.

One thing was for certain, she was not going to be a starving artist.

Probably just starving.

But May wasn't thinking about that right now.

She yelped a bit when she felt someone place their hand on her shoulder. She turned to see a boy with a gentle smile on his face.

"Sorry if I scared you. I couldn't help but overhear, but there are other things besides sketching, you know," a boy she was not familiar with said. "There are different kinds of art: sculpting, painting, 'modern art'… maybe you might want to try that?"

"Well, I'm not too good at any. Believe me, I tried them all," May politely explained. "But thanks."

"If anything, we have art lessons every Monday if you would like to stop by for that. It will be a lot of fun and you really learn a lot. You will be good in no time! Anyone can learn. Oh, and I'm Tracey by the way," Tracey added, taking his hand out to shake hers. May smiled, taking his hand.

"I'll see if I can, thanks, Tracey! I'm May!" May greeted back. She continued to smile until Tracey walked back to his seat.

May grinned as she snuck out of the art room.

Yeah, maybe she'll come back on Monday.

Or maybe not.

.

 **Tai Kwan Do**

"What was I thinking!? Forget this, I'm out of here!"

.

 **Culinary club**

"Hey, this isn't so bad, this will be fun to try. I love cooking too!" May exclaimed, forgetting the fact that the last time she helped out in the kitchen, she nearly burned the kitchen down. Someone tapped her shoulder and she jumped a bit. May's eyebrow twitched, wondering what it was with people sneaking up on her all of a sudden.

"Hi, I'm new to this club too. I'm Serena!"

"I'm May, nice to meet you!"

"Likewise. So what are you thinking of making?" Serena wondered. May shrugged.

"No idea, to be honest. I'm really new to this. Well, I mean I help my mom around the house, but other than that, I haven't cooked much." Serena nodded. May didn't noticed someone was behind her.

"I couldn't help but overhear," someone interjected. "But you should start off easy with a cake or cookies. Those are always fun."

"That's a good idea, Brock," Serena said.

"Nice to see you here, Serena. And what's your name?" Brock asked, turning to May. May smiled.

"I'm May. Thanks for the suggestion," May said.

"Well, if you need any help, I'll be over there, I need to finish up the goodies I've been baking. I'll be back though," Brock said before heading back to his side.

.

May looked around, watching everyone know what they were doing. She frowned.

"Oh man, I wish I knew what to do," May said.

"Hey, don't worry if you're not the best right now. We all have to start somewhere." Serena grabbed an index card. "Why don't you try baking cookies? Here's the recipe!" Serena said. May smiled gratefully.

"Thank you so much!" As May started adding the ingredients into a bowl, she looked over to Serena stirring something up. She was amazed by the way she was able to cook so well.

"You're so good at this! Are you sure you're new here?" May questioned her suspiciously.

"Well, I've been cooking before. I would have come here sooner if I wasn't racing all the time," Serena began.

"You're on the track team?"

"Yup! But- between you and me, I hate it! So… a friend, talked me into ditching track," Serena explained. May smiled, and then thought of her own running regimen. She sulked.

 _I wish there was a way to get out of running too,_ she couldn't help but think. She shook that thought away, realizing that was no way to keep thinking. She had to remember her goals: crush Drew.

"Would anyone like some of these pastries I made?" a boy named Brock asked. He made his way towards May, offering some.

Her mind wandered to the pastries in front of her, completely forgetting her previous train of thought.

"But in the meantime, don't mind if I do!" May exclaimed, plucking a treat Brock offered from the platter.

"I see you like my desserts," Brock said, smiling.

"You bet I do! They're delicious!" May exclaimed.

"Why thank you! You can have more if you like," Brock offered. May's eyes light up, feeling as though she was in heaven.

May smiled, "I think I'm going to love this one!" And so, May continued to look at the recipe and try her best to make the most delicious cookies she can!

.

"Oh no," May whispered to herself, panicked. She had a ringing in her ear, and that was from the sound of the school alarm.

"Okay, okay, everyone stay calm, let's evacuate calmly!" Brock shouted in hopes they could hear him over the alarm. Everyone rushed out the kitchen, afraid. Brock quickly grabbed the fire extinguisher and used it to stop the flames. He sighed, thankful that the only thing that took the brunt of the flames was the oven.

"Woops," May thought, biting her bottom lip as she thought back to what happened in the kitchen. She was glad everyone was safe.

She didn't think she'd burn the kitchen down… _again_.

"Uhm, sorry you guys. I thought I set it for 30 minutes," she said to the culinary club. She frowned. "I was being careless." And May loved the delicious treats everyone shared, too. However, the students apart of the culinary club must have been incredibly accepting and understanding, for they simply smiled and laughed.

"Don't worry, it should be fine. That oven is the oldest one anyways. We need to replace it," Brock said reassuringly.

"But… maybe this isn't for me after all," May thought, realizing the trouble she caused everyone here. And to think, she thought she was beginning to find her niche.

"I guess I'll try again tomorrow…"

.

Today's practice made May fall to the ground by the end of it, her legs sore after another strenuous basketball drill. This time they were working on her agility.

"This is torture," May heaved, exhausted.

"Hey, you're doing really well! Don't give up, you got this!" Ash reassured and tried to cheer her up. He extended his hand for her to take.

"I wish. Why does it feel like I'm not getting any good?" May asked with concern.

"Maybe because it's barely been a week," Ash reasoned, laughing at her ridiculousness. May sighed.

"I guess. But do you think I'll be good in time for try-outs?" May asked. Ash grinned. "I barely even dribbled a basketball yet."

"Well, it's barely been a week. It's only the third day! Plus, you don't finish your warm ups in time. Don't worry, you will be great I'm sure! I noticed that the practices we've had really improved your stamina! You just can't give up, May!" Ash said inspiringly.

"Thanks, Ash." May sighed, grabbing her backpack and walking home.

.

That night, May was rather quiet at dinner. Her parents looked at each other with concern. Usually, May was the most talkative. Tonight, she seemed way too quiet. Her appetite was not as big as usual, either. She only picked at her food.

"Is something wrong, Honey?" her dad asked.

"Yeah, you seem more quiet than usual," Caroline added.

"Also, you are coming home later and later from school," Max continued. May sheepishly laughed.

"It's nothing, it's nothing!" May reassured. "It's just, I'm thinking of joining the basketball team is all," May said nervously.

"You…. Playing a sport?" Max asked incredulously. They all looked at her with confusion. Max especially looked confused, before bursting out into fits of laughter.

"Honey, you never showed any interest in sports before… is it for a boy? Do you have a crush?" Caroline teased.

May blushed, "Mom! No way! I just want to do more stuff is all! I am even planning to join another afterschool activity! I was considering art or culinary club, but I still need to find something."

"Wow, that's great you're getting involved, May!" Norman said. "Hey, you know, if you need some help, you know your old man can help you out!"

"Gee, thanks Dad. But I am already getting help afterschool." May couldn't help but think how long it's been since her dad played basketball.

"Are you sure?"

"Yeah, I'm sure!" May laughed. She sighed, ready to finish her homework before getting to bed. May brought her fingers to form a square and had them over her eye.

"And so, the journey continues with May's Expedition! Will May find the perfect afterschool club? Only tomorrow will tell!" May announced.

"Wow, what a dweeb," Max said from her door.

"Hey, get out!" she yelled before throwing a pillow at him. Max closed the door before it hit him. She sighed, shaking her head at her little brother before she got ready for bed.

.

 **Swim Team**

It was a new day, and May was planning to test her luck by going to more clubs. She was in a one piece swimming suit and a towel wrapped around her torso.

May looked over to the pool, excited to start. She looked over to the pool and saw a girl with fiery orange hair. May watched as she dived in and began moving through the water.

"She's… amazing," May complimented, her eyes following Misty's quick and elegant movements in the water. If she didn't know any better, she would mistake her for a mermaid.

"Wow, maybe I can get that good," May said to herself. She moved to the end of the pool where the swim team's coach was.

"Hello, I'm May Maple and I'm ready to be a part of the swim team!" May announced.

"How fast are you?" the coach asked.

"Um, fast? I'm not sure," May admitted, sheepishly chuckling.

"Well then, let's get you ready to try out then, let's hope you're good." The coach was intimidating May. She gulped, afraid of the scary coach.

"T-try out?" May stuttered. Her bubbly attitude quickly deflated at those words. She began to sulk. "You know, actually, I think I got the wrong team, I meant to try out for the… Urhm, bowling team!" she continued to laugh all the way to the locker room, with the coach looking extremely confused.

In the locker room, May frowned as she took a moment to ponder of what she was to do now.

.

 **Nature Club**

May tilted her head, confused.

"I don't get it. You just climb trees?" May wondered. Iris shrugged.

"I was forced into joining a club, so I figured I'd make my own club," Iris said, smirking as she closed her eyes and laid down.

"Hey, I can get used to this," May said as she laid down under the shade of the tree.

"Although… I didn't think anyone else would join…" Iris said aloud, looking at May pressingly. May frowned, feeling the tension.

"Okay, okay, I can take a hint." May sighed, hoping to find a new club.

.

 **Dodge ball**

"This… was… a bad idea!" May shouted before she got hit in the head.

May cried, "Why do I always get hit in the head?"

.

Dawn was a bit embarrassed at tryouts.

She loved cheerleading. It was fun and felt like gymnastics in a way, but cheerleading involved more team effort and she loved cheering people up. But she didn't know they would have practice right next to the boys practice!

If she messed up, they could potentially see. If she falls on her butt, they could start laughing.

Dawn did not like the sound of that, especially in front of the major athletes.

"No need to worry," she whispered to herself, closing her eyes to get rid of such thoughts.

However, what happened in practice today was unexpected.

Dawn's eyebrow twitched.

"Are we… really here to cheer Gary?" she wondered, more than a bit annoyed.

She was a bit relieved, for herself, that she would never fangirl like them for someone like Gary. At the very least, if she ever did, she would do it a little more covertly, and not for Gary, of all people. She didn't know him personally, but she had heard many stories from numerous girls about how much of a player he was.

She watched them cheer for Gary instead of practice. She looked over, and she was surprise to see Gary Oak was actually staring at her. His features, she had to admit, justified – a little bit –why they would easily fell for him.

However, that didn't justify why they would be cheering so much for one guy.

Gary smirked, walking over to her.

"Hey, you're new, aren't you? And you're not all over me. We can fix that, if you want. Here, I'll let you give me your number since you're very pretty," Gary said with a charming smile.

Dawn was not amused, nor fazed by his attempt to ask her out.

"Who said I want to give you my number?" She glared at the boy, crossing her arms. She was beginning to suspect what she thought was true: the top athletes all were amazing at sports, but have fatal flaws. She suspected this must be Gary's: lame pickup lines. At least, to her. The other cheerleaders were gushing at every word he said.

"You don't like compliments?" he asked. "Because I'm not a photographer, but I can picture me and you together." When Gary said that, Dawn couldn't help but cringe. "Geez, that didn't work? You must be something special," Gary chuckled. Dawn couldn't help but think it wasn't something else, his pickup line was just incredibly lame. Was that apart of his plan? Dawn made no effort to laugh with him. Gary shrugged. "I mean, we should definitely get to know each other, seeing as you're new to the team and all."

"Give it a rest, Gary," a familiar voice interjected. Gary sighed, his eyebrow twitching at Ash in back of him, interrupting.

"Ashy-boy, grownups are talking so why don't you just mind your own business."

"Why don't you know when to give it up? She's not falling for your dumb pickup lines," Ash countered. Dawn giggled, relieved that she wasn't the only one who found his lines falling short. Gary sighed, looking rather annoyed. He turned towards Ash, ready to get in a fight if need be.

"Look-"

"Gary! Ash! Why am I hearing your mouths moving and not your feet? Get over here and give me 20!" their coach yelled from the distance. Gary glared at Ash.

"Thanks for nothing, Ashy-boy. I'll see you again, Missy," and Gary ran back to the coach.

"Hey, thanks for that," Dawn said gratefully. Ash grinned.

"No problem! Gary's not so bad once you get to know him, he just comes off strong at first," Ash explained. "But hopefully he doesn't bother you again. I got to go, good luck!" Ash waved goodbye before running back to his team.

Dawn gently smiled, thankful for one Ash Ketchum.

.

After practice, Ash hurried to the basketball courts outside. He arrived to find an exhausted May. He was shocked.

"Hey, did you start practice without me? Wow, I'm actually impressed!" Ash said, giving her a thumbs up. He never expected her to practice on her own. May sheepishly chuckled, wishing she actually did end up practicing.

"Actually," she paused, twiddling her fingers. "I've been looking for an after school activity because boy, waiting for you sucks so much! I have been looking and looking for different clubs that are good! But I don't know any good ones! All the ones I tried are just not for me." Ash's eyebrow rose.

"Uuuuh, May? Why don't you just check the bulletin board?" Ash wondered, confused.

"Wait, there's a bulletin board? I didn't realize there was one!" May laughed cheekily. Ash sweat-dropped.

"May… you're really weird," Ash couldn't help but admit.

May giggled, "Well, who's worried about that? I'll look into that whole bulletin board thing tomorrow! Let's just focus on practice!" Ash nodded, happy that she seemed more motivated.

Either way, May continued to work hard, counting down the days till tryouts.

.

 _AN:_ Woohoo! Another chapter down! I want to apologize for the short chapter, the next one will be longer. It's just when I was planning these chapters out, I didn't think everything I wanted to write would be short haha. Plus I wanted to introduce more characters in this chapter. Next one will be longer!


	4. Fallen

_AN:_ New chapter here! Woohoo! I hope you guys enjoy! I hope everyone had a happy New Years and like this chapter, because I had so much fun writing it! x)

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Chapter 4:  
 _Fallen_

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May found herself in a routine for the next few weeks. She would wake up early morning, to her displeasure, and go for a run with Ash around the school. Ash would constantly encourage her to keep up, so she can get used to it and increase her stamina.

She felt as though she would never get used to it. However, although she didn't notice it herself, Ash realized that she was slowly but surely getting the hang of things.

May did not complain anymore about waking up so early, for it has been engrained in her head now. It has become habit for her to simply wake up in the early mornings, before the sun rises, to go running. Ash didn't have to slow down so much now, May starting to keep up with him when it came to a slow trot.

Ash was pleasantly shocked, that when it came to keeping her stamina up and increasing her agility, which they have been working on since their first day, May had significantly improved.

The best part, was that she was getting so used to the habit, that she was now becoming more disciplined when it came to practice. She would put in effort that he hadn't seen in her before. When she would get something wrong, and he would correct her, she did not complain (as much) or he would not see the hint of annoyance expressed on her face when he would tell her so (more or less). She instead nodded, continuing to practice and take his criticism seriously (that didn't stop her from grumbling a bit from time to time). Nonetheless, it was still a big improvement.

Not to say she still had some long ways to go.

Because, she had some _long_ ways to go.

In the morning, May ran with Ash. She would then head to school and shower there, changing and heading straight to class. After class, she would talk to Dawn for a bit, before she went to an afterschool club she would dabble in from time to time, still trying to find a club that fit her. Then, she would meet with Ash and warmup by either running to and from the ends of the basketball court, or doing a quick exercise. Next, they would focus on drills, from shooting drills, to dribbling drills, to passing, or learning about rebounding, etc. Ash would take moments to explain to her what all of that meant, the different positions players are, along with what position would be best for her.

"What position do you play?" she asked one day during practice.

"Well, I can usually play whichever position needed at the time. But they generally need me as shooting guard or point guard when it comes to offensive plays," he told her proudly. She nodded. He thought for a moment.

"If I were to guess, you would be… center at the moment."

"I want to be the one who makes all the shots," she told him.

"Well then that means you would need to practice more shooting drills," Ash thought aloud, already trying to figure out the best approach for her. "But even so, you should still learn how to do it all, you know. That way you will for sure make the team!" May nodded, excited. This pumped her up more, her fist clenching with anticipation.

Things were looking up for May, for sure. She felt like her life was turning around for the better. They would always end practice with a one on one game. This was May's favorite part, because she could actually take those drills and use them in an actual game.

Who knew basketball would be so fun.

Not to say she could beat Ash in a match. Not even close. But it was still fun, filled with laughter and happiness as she continued to improve.

In the back of her mind, she was excited to serve Drew in a match, thoroughly defeating him some day.

While May was rather happy, improving and loving her time practicing (except when it was exceptionally hard), Ash could not say the same thing.

Not to say he was unhappy, however, a better term for it would be _sleepy._

Just sleepy.

However, he found himself pulling through, his own discipline and determination as unrelenting as ever. Ash, unlike May, already held a full schedule before he decided to help her. He had agreed to simply give her pointers, but he ended up getting way too engaged and determined without even realizing it. He soon became a coach in his own right, guiding her and making sure she was doing the drills correctly. He even made list of the foods that will help give her more energy throughout the day, along with creating a full out schedule for her to follow.

When Ash helps someone out, he really helps someone out, doing everything he can to make sure they were doing well and got the assistance they need. He was proud that she improved so much, however, he found the more he invested his time, the more he didn't have to do things he used to do.

Like homework. Or studying. Or sleep.

Well, he would still do them. He was not completely daft. However, he found himself lacking in the sleep department more and more each day.

.

Ash found himself slipping in and out of slumber during algebra 2 class today, which has been happening a lot recently. The hard wooden desk was usually very uncomfortable to sit still in for him. However, today was very different. Today, the hard desk top felt like a pillow as his chin rested on it. His desk was still very uncomfortable for him. He usually would much rather run or do something, than stay seated for so long. However, he found his need for sleep was far more important today.

The professor was lecturing about something on polynomials, but he was too tired to panic and worry. All he heard was his professor's voice muffled, while all he could see through lidded eyes was the blurry figure of his teacher at the dry-erase board, writing some math equation down.

He constantly told himself to sit up and pay attention, but his will power was lacking today, his eyes finally closing.

It was only until Serena tapped his shoulder, that he jumped awake, flailing his arms and giving a sharp yelp. The whole class giggled, and his face heated with embarrassment. He wiped the bit of drool that was running down his chin.

He stared over to the professor, who merely paused to give him a disappointed look, before continuing with his lecture.

He slumped into his desk, never feeling more embarrassed and so guilty for making a ruckus in class. The look his teacher gave made him feel worse.

"You should pay attention, Ash," Serena warned. Ash looked back to her, smiling and nodding.

"Thanks, I will," he merely said before turning to the dry erase board and copy the equations.

He only wished, he knew what they all meant.

.

Ash was hoping he would be able to make it out of class without facing his teacher. When the bell rang, he realized there would be no such luck for that.

"Ash Ketchum, we need to discuss your grades," his professor said. "Stay a moment."

Ash gulped, scared for what he was going to say. He knew he was slowly falling behind. The last two practice quizzes were represented of that.

"The results of the most recent practice quiz is very concerning," the teacher began, passing him his quiz.

He looked, and his eyes widened at the score. 55.

"Oh man," Ash said, disappointed. Before, he had managed to keep his grades up by studying extremely hard and focusing on school after sports. However, he found himself studying less and less these last few weeks. He bit his lip, staring at the grade. Even back then, when the first practice quiz came, he brushed it off because he figured he wasn't doing _too_ bad. Sure, he received a few C's, and even the last D drew up some red flags, but he never thought he would fail a quiz. He hoped this wouldn't represent his test score in the future. "I really need to study."

"Yes, you do," the teacher agreed. "I noticed you've been sleeping in class as well."

"Yeah, sorry about that. I guess sports has been taking up a lot of time recently," he sheepishly laughed.

"Yes, I understand you are an athlete who cares about your games more than school at the moment. However, your grades are also very important. If they slip any more, then you won't be able to play any sports for the whole year," he reminded. Ash gulped, understanding fully what it would mean if he didn't bring up his grades.

This was bad.

Extremely bad.

.

May noticed Ash wasn't as he usually was. He had a big frown plastered on his face throughout their entire practice. He didn't even stifle giggles when she cracked hilarious jokes (she swore, she could be a comedian some day).

She tried to focus on her exercises and drills, but she kept on watching Ash, because he seemed so sad.

After doing another drill, she looked over to Ash, who was on the bench. Her eyes widened when she noticed his eyes were closed shut.

"How… can he sleep sitting up?" was the first thing on May's mind. She scratched her nose, confused. That would have been impossible for her.

"Ash?" she asked. She was kind of afraid to wake him up.

"He's not usually like this, what's going on?" she wondered, crossing her arms and tilting her head. She shook him awake, and he yelped for the second time that day, waking up with a fright.

"Ash?" she called again. He frantically looked around, wondering what was going on.

"W-what? D-did you finish those drills?" he asked.

"Well, if I didn't, there's no way you would know," she teased, sticking her tongue out. He rubbed the crust out of his eyes, but soon laughed.

"Well, that just means you're going to have to do them again," he said, and May scowled, wondering why she even brought that up.

"Well, he seems normal now," May mumbled, annoyed as she stomped her way back to the basketball court.

She should have known better.

.

"Hey! Ash! I purposely did this wrong, and you didn't even critic it!" May noticed, referring to the dribbling drill she has been doing for the past two minutes. Ash placed cones on the concrete in hopes she would be able to avoid them, along with dribble effortlessly. He taught her the best way to do so, telling her to not look down at the ball, and how her eyes needs to look at her surroundings. She remembered him lecturing that she always has to be surveying the area, and how it might be fine now, but it will be harder when there are opponents blocking her way.

She was looking down, making simple mistakes that he would usually catch and berate her for, yet she didn't hear him say anything today.

Ash stared at her curiously.

"Oh, you did that on purpose? That's how you always do it, anyways," Ash said, scratching the back of his head. May fumed, extremely annoyed, however, did notice he seemed extremely blue compared to how he usually was. He didn't smile as much, and he seemed as though he was deep in thought all the time. She may have done those mistakes all the time before, but he usually loves critiquing her and correcting those mistakes as soon as she does them.

"Ash…" she trailed off, trying to find the best way to ask him. He seemed so down, she was curious as to why.

"May, you're supposed to be practicing your dribbling." May grumbled, but soon glared at him, stomping her feet and clenching her fist.

"Well I can't concentrate when you look so down! What's wrong?" she asked, her hands on her hips as she stared at him, in hopes of reading him. She seemed angry to him, but in truth, she was really only concerned for him. Ash frowned, debating how he should say it. He sighed.

"Okay, well, the truth is, I've fallen behind in math," he confessed, his body slumping as his head fell low.

"Really? I mean, that's not the best, but you can always catch up, right? And even if you don't, it would just be that one class, right?" she tried to reason, hoping it made him feel better. Unfortunately, it didn't.

"That's the thing, I can't afford to fall behind in any of my classes, especially math. If I do, then I won't be able to play any sports for the rest of the year!" Ash explained, exasperated. May gasped, frowning too. No wonder he was so down. Being an athlete was his life.

"I'm sorry, Ash," she apologized. Ash shook his head.

"Don't worry about it, it's not like it's your fault," he said. May frowned at this.

"But…" she trailed off, feeling an immense amount of guilt. She never heard of him failing until now, until he started training her. He told her it wasn't her fault, but a part of her felt like it was entirely her fault, and now, her responsibility to fix this. Ash did so much for her, she had to return the favor. She had to help him somehow.

There was a lot of silence, while May contemplated how she would be able to help Ash with his predicament.

She then grinned, excitedly. She looked at Ash, her eyes gleamed with hope and determination. Ash raised an eyebrow, wondering why she was looking at him the way she was so suddenly.

May looked fired up, prepared for anything.

"Okay! Here's the deal! I will personally tutor you after school, and then we can practice! That way you will have time to study and we can train!" May suggested.

"But May… you need all the help you can get, are you sure? I don't think you should cut back on practice time." May smiled, waving him off.

"Don't worry, don't worry! It will be easy!" she reassured him confidently. Her hands were on her hips as she gave an eager pose. He raised an eyebrow, confused by her odd mannerisms and gestures. He wasn't sure about this.

"But, May… you're like, really bad still," Ash admitted. May deadpanned.

"Geez, thanks for believing in me," she mumbled, crossing her arms. "But still! I am going to be the best tutor ever!" May boasted, reassuring Ash.

"Are you sure?" he asked, his eyes hopeful. She nodded proudly and cockily.

"It's the least I can do!" May smiled, happy she could help.

He was surprised, but truly thankful.

"Thanks, May!"

.

"What? But… May, how are you going to tutor Ash when you get average grades at best? You hardly study yourself," Dawn argued, shocked by what her friend was telling her. They were once again in the cafeteria, eating their lunch at their usual table. May crossed her arms, leaning into her chair.

"Hey, I can do it. I remember all kinds of stuff from our class! I just have to pay attention more! I'll find a way!" May retorted.

"I'd also like to point out that you're just a sophomore while Ash is a junior! That means he is in algebra 2 while you're only in geometry!" Dawn pointed out.

It took a moment for May to officially freak out, almost falling out of her chair.

"Wait, really?" May yelped, afraid and panicking. Her hands went to her head as she tried to scramble for a way out of it. Her mind was reeling, wondering what she was going to do now. She had told Ash so confidently and reassuringly that she would help him, but how was she supposed to learn everything about algebra 2 before she was supposed to tutor him? "What am I going to do?" she screeched.

Dawn frowned.

"I don't know, but I'm sure sports mean everything to him. If he doesn't keep his grades up, he won't be able to play them. If he told you that, then that means he might be in big trouble. May, if I were in your position, I would be honest with him," Dawn told her, not liking the idea of seeing Ash fail, especially after how much he helped her and was so kind to her. Really, he was kind and sweet to everyone. She would hate to see him fail because of this misunderstanding.

May's eyes dropped to her uneaten food, for once, not feeling so hungry. She gulped.

 _"_ _What am I going to do?"_ she thought. She didn't want to let Ash down, she wanted to be the one to help him after everything he has done for her. He got so involved and so engaged in helping her with basketball, she had to find a way to help him with his studies.

Her eyes stared at her uneaten food, determined. She quickly stood, standing proudly.

"There has to be a way, and I will find it!"

Dawn merely sweat dropped, hoping what she said was true.

.

May decided to try her hardest, the hardest she has ever tried before when it came to school. In the back of her mind, she wondered why she was so eager to help in school without realizing at the time how exceptionally _bad_ she was at it.

Come to think of it…

She never really paid attention in most of her classes.

"Maybe I should have…" May thought aloud, her index finger to her chin as she contemplated. Dawn was right, her grades were average at best. But it was never really important to her. She would only really pay attention when it was something interesting to her or if something funny happened in class.

"Well, just because I didn't pay attention before, doesn't mean it's too late for me now, right?" May nodded to herself, deciding it was a good a time as any to at least try in school.

But first…

She will conquer algebra 2!

.

She found herself in the library, grabbing every Algebra 2 book she could find and trying her best to study, reading over the chapters. Her eyes were still brimming with determination and conviction.

"I have to figure all this out. I have to learn this and quick. Otherwise, Ash might fail!" May mumbled as she continued to read through the first page of the textbook.

May found it extremely hard to focus, getting distracted over every little thing.

"Oh look, is that who I think it is?"

There were some distractions she would rather live without. She growled, glaring at the boy walking towards her.

"Drew? What are you doing here?" she questioned, gasping. Drew brought his index finger to his lips, making a shushing noise.

"This is a library, you know. I know you have never been in here before, but you're supposed to be quiet," he started, smirking at her annoyance.

"Why you-"

"Actually, to be honest, I'm really impressed that you would even step a foot in here. Why are you here of all places?" he wondered, genuinely curious. He's generally in here a lot, finishing his homework and his studies, but had never once seen her here.

"None of your business!" She glared, stomping her way to a different desk. Drew eyed her curiously before sighing, shrugging, and then walking back to his desk.

May continued to study algebra 2. At least, she tried to study. She felt it was incredibly hopeless.

"I can't give up now," she whispered to herself. "I need to study this. It's mind over matter. If I think it's easy, it will surely be easy!" she said, her fist clenching and fire in her eyes. She reviewed the chapters again, however, all the signs and symbols looked so foreign to her. "I really wish I paid attention in all my math classes," she thought, her head banging against the book.

"Heh, figures you'd just come here to sleep," Drew said, chuckling at the girl a few desks away. May immediately rose, glaring at the boy. She didn't worry about the red mark on her forehead from the book, for she was too preoccupied thinking the best way to tell Drew off.

"Well, I'd like to see you try and do these problems!" May challenged, crossing her arms and smirking. Drew ended up walking towards her again. He eyed her book, intrigued.

"Oh, that's a piece of cake," Drew said, grabbing the pencil in her hand and the piece of paper on the table to quickly write down his work before scribbling the answer down.

It didn't take him long to complete a question that was driving her crazy for the past hour.

May's eyes widened, shocked.

"H-how… why… Wait a minute, how did you do that?" she asked, and Drew shushed her again, reminding her that she was in a library. He smirked afterwards, shrugging nonchalantly.

"It's easy, we're learning that in Algebra 2 right now," he said. He raised an eyebrow, eyeing her suspiciously. "But there's no way someone like you is in Algebra 2, though. Why are you studying this stuff?"

May glared, annoyed with his questions and the fact that he was better at her in this subject. Figures, Drew was able to get into the advanced class.

"As if I'd tell you. Like I said, it's none of your business," May spat, crossing her arms and looking the other way. Drew shook his head, shrugging.

"Suit yourself," was the last thing he said before he walked back to his table to go back studying.

May grew incredibly frustrated, looking at what Drew did on the paper, and trying to use that to understand the other questions in the book.

"Oh, this is no use. I give up!" May whispered, annoyed. She looked at Drew, eyeing him inquisitively. She looked back to the Algebra 2 textbook, a melancholy expression etched on her face.

She felt terrible for saying she would give up. She thought about Ash, who always smiled at her and was so patient with her for the most part (except when he could be harsh during practice, but that was besides the point). He helped her so much, and he never gave up on her, which was a miracle in of itself.

He spent so much time with her on basketball drills and assisting her, how could she even think of giving up on him?

 _"_ _Ash, I don't want to let you down_ ," she couldn't help but think, her eyes brimming with tears at the thought. _"You've done so much for me, and, I just wanted to…"_

She sighed, wiping her tears, and staring at Drew. No matter how much this pained her, no matter how much it would hurt her pride, she knew what she had to do. She was on a mission and she would _not_ give up.

She made her point by abruptly standing up from her chair, causing Drew to look up at the noise. He was shocked to see May staring straight at him. He felt a little weirded out a bit, wondering why she was looking at him like that.

She was acting so _strange._

He stared at her blankly, confusion all over his face.

He saw her take a deep breath in, and another out, before marching her way over to him, never once breaking eye contact.

"M-May?" he wondered, absolutely confused by her actions. It wasn't till he said her name, that her eyes shifted.

May's eyes were diverted to the ground, not wanting to look him in the eye as she asked him such an embarrassing question. Her cheeks never felt rosier than now, as she mustered up the courage to ask Drew for help. Yes, _help._ She was surprised herself.

"Drew… Look, I'm…" she trailed off, never once being able to say this to him. Never once knowing she would be in this position. "I'm sorry about what I said before. Truth is, I was just jealous that you were already in Algebra 2 and knew so much, but I'd like to learn more," she admitted, her face heating from the sheer embarrassment. Here she was, being vulnerable towards Drew, her biggest enemy and rival. "C-could you help me? I'm having a lot of trouble with this problems," she confessed, feeling absolutely torn and just _weird_ for doing this.

Drew sat there, his eyes wide open as he did not expect her to downright ask for his help and be so straight forward about it. Never had he seen May this vulnerable, after all. It seemed so foreign and just so out of place, he wasn't really sure what to even say in this situation. He was so used to their teasing and banter that went back and forth, he didn't realize what he should say when May was being completely serious and nervous and embarrassed like this.

"Wait, really?" he asked incredulously.

"What?" she asked defensively.

"N-nothing, just didn't expect this, is all." Drew shook his head, still not believing this. After he hadn't given her a full answer, May sighed, a bit annoyed that she had to be honest with him for nothing.

"If you're busy, then I'm sorry for bothering you," she began, but Drew stood, catching her attention. He smiled, albeit a bit uncomfortably and unsure of himself.

"Actually, I have time. I actually needed to finish that homework anyways and review it. So if you want me to explain some stuff, then I'm cool with that." Drew shrugged, his voice nervous as well, this situation feeling so out of place and something he never expected having to deal with.

May grabbed her things from the other desk and sat next to Drew, looking at the book he was pointing at as he explained what he did.

After some time passed, May looked at her hands, squirming a bit, unsure how to say what she wanted to tell him.

"H-hey, Drew?" May began, averting her eyes from him. They instead were staring at the algebra 2 book.

"Hmm?" he hummed, taking his eyes away from the book to look at her.

"T-thanks… for helping me," May finally thanked.

"Um, no problem."

There was a long pause, before Drew went back to teaching May all about functions and polynomials.

.

 _AN:_ Here you guys go! Thanks for all the support! Haha, this was one of my favorite chapters to write! I feel like May is really developing as a character here, at least that's what I was going for! Please, let me know what you all think! Hopefully this chapter was good and funny, and also sweet! xD Until next time! Hopefully soon!


	5. Agreement

_AN:_ Okay, you guys, here we go, a new chapter up! I hope you guys like it! X) This is the kind of chapter I was talking about when I said I was going to add a lot of characters interacting. If you catch any grammatical errors, please let me know! Makes it easier for me to fix them! I don't have a beta so it helps a lot! Enjoy!

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Chapter 5:  
 _Agreement_

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"You're really worrying all of us, you know," Serena admitted, clutching her books to her chest. "You've been sleeping in class and you haven't really been yourself lately," she added. Ash frowned, looking at his feet.

He felt really bad. It's true, he hasn't really been himself. He found himself sleeping at times he shouldn't be, for the most part. At lunch, he would gobble up his food, of course – no point wasting a meal – and would soon find his eyes closing as he was off to dreamland.

Ash averted his gaze to the floor in shame.

"I'm sorry, I don't mean to worry you guys," Ash said, scratching the back of his neck. They continued to walk to her locker so she could drop off her books. "I just had a lot of stuff I have to deal with. School, practice," he explained. She nodded, already understanding. Academics didn't come naturally for Ash, so she understood how he would need more time to study. And knowing Ash, he would work hard when it came to practice. He would always give it his all, giving 110% every time. It was no wonder he would be so tired.

"Yeah, I get that. That's why, if you need anything at all, please, let me know!" She gave him a reassuring smile, and Ash nodded, truly thankful. He grinned.

"Thanks a bunch, Serena!" he said.

"I mean it, Ash! You don't have to put all this stress on yourself, you know. I mean I'm sure we can help tutor you if you're worried about grades. And if you need a break, all of us can hang out again like we used to," she said, hoping to get through to him.

"I'm not putting it all on myself, don't worry! I actually already have a tutor, so you don't have to worry about that!" Ash tried to reassure. "Also, promise, we can all hang out on the weekend if you guys are up for it!" he promised. He then heard a beeping from his watch. He looked at it, and was surprised practice was already about to start soon. "Ah, sorry I couldn't talk more right now, but I have to go or else coach is going to kill me!" Ash explained, waving goodbye before running off to the gymnasium.

This left Serena to ponder, wondering who his tutor was, and if he was really going to be okay.

She sighed, knowing Ash would do whatever he can to make everything work out.

She hoped he meant what he said when he said he was okay. Either way, it was the end of school and time for after school activities.

She was planning to go to culinary club again this week, along with a new club she thought would be interesting, too.

Definitely beats track, at the very least.

She beamed to herself, excited for the rest of the day.

.

Studying, May was surprised to say, went great.

For once, she focused and Drew made it easier for her to understand, surprisingly. As much as she hated to admit it, he actually was a really good tutor. He even went back to explain things she hadn't even learned in her algebra one class (what she was asleep for). It was a big help, and she found herself being able to work the problems by herself (for the most part).

"Wait a second, so for polynomials, what about that foil method you were talking about?" she asked, her eyes staring at the textbook with a concentration never seen before in her eyes.

"That's easy, just have to remember the rules, you know? Here-" he started, writing down a mnemonic. "If you have trouble, just use this." May nodded and thanked him, continuing to work on the problem with the mnemonic given.

"By the way, can you tell me why exactly you're learning algebra two work now?" he asked. She paused, contemplating for a moment.

"W-well… I want to help someone out," May said. "I'm afraid, this is the only thing I can do to help them. They have helped me so much, I have to be the one to help them." Drew looked at her oddly, wondering how she did logic in her mind.

"I mean, I guess so. But there are other ways to repay someone, you know," Drew reminded.

"Yeah, I guess that's true. But…" she shrugged, not sure how to put it. She tapped on her chin for a moment before staring at Drew and giving a confident smile. "Well, it's hard to explain. But I just can't let this person down, by no means."

"You always were too stubborn for your own good," Drew said, a small laugh coming out. May glared at him, but soon shook her head.

"I'm not stubborn!"

"Yeah, you really are. Now come on, stay quiet, we're still in a library," Drew reminded. May blushed, looking around and embarrassed at the faces staring at her.

"Right. Just… please, check my work," she said, hoping to change the subject. Drew nodded, doing just that.

.

It felt like such a long time for her. But she still kept at it, algebra finally making some sense to her.

"May?" he asked, his voice surprising her by how light and gentle it was. Really, this wasn't the Drew she was accustomed to. It really creeped her out, actually. She gulped.

"Yeah?" she asked. She looked towards him, and noticed his eyes were still fixated on the book, seeming too concentrated on the equations to feel her gaze on him.

"Don't tell anyone about this. I _do_ have a reputation to hold," he said, eyeing her from his position and smirking at her. May instantly grew annoyed, her fist clenching.

For a second there…

She huffed, sticking her nose up and furrowing her brow.

"As if I would tell anyone about being around you for longer than a minute!" May crossed her arms, turning away from him. Drew laughed, happy they could be themselves again instead of being so, _so_ awkward.

"See you around. And if you do come by the library again, I'll be here, just so you know." His keychain swung from his finger, making circles in the air.

May looked back, and then smiled thoughtfully.

"Thanks again," she said gratefully. Drew simply waved as he walked away from her. May soon looked over to the clock, noticing the time. She grinned.

"As much of a prick he can be sometimes, he's actually… really helpful," May thought, her lips forming a smile at the thought. Really, she was still in disbelief at the whole ordeal.

She soon shook her head. "No time to think about that! I have way too much to do!" May said aloud before she raced towards the computer lab. "Since when did my schedule get so full?" she sobbed, cherishing the days she could laze around.

.

"Aren't you usually off somewhere by now?" Gary wondered curiously. He would never admit it, but Gary did find it strange how Ash was acting more recently. When he would think up some great ways to tease him, he would just either take it or not care.

"Yeah, you're usually running off after practice, like every day," another guy pointed out. Ash just shrugged, before grinning.

"Day off," he said. Many of the guys looked at him oddly.

"You got a job somewhere?"

"Well, no, not really. Eh, maybe, sort of, I guess?" Many of the guys in the locker room stared at him curiously. He wasn't sure what to say, knowing he was supposed to keep quiet about their little agreement. So a job would be a good excuse for his leaving, either way. He decided to stick with that, figuring it wouldn't hurt to not say anything. He simply shrugged, yawning.

"Whatever. No wonder you're so tired. You should take the time to nap or something, otherwise coach is going to take it out on all of us again," Paul said, his face stern and his eyes serious. Ash nodded, feeling rather tired. He yawned, not realizing how tired he was until someone said so.

"Yeah, I'll be sure to after I finish my homework," Ash said, before leaving the locker room.

He was surprised to see Dawn waiting outside the locker room.

"Oh, hey! What're you doing here?" he wondered, noticing she was still in her cheerleading uniform.

"Ah, well, May told me what happened – with your math grade. I just wanted to make sure you're going to be alright," she said.

"Yeah, I'm having a lot of trouble with algebra 2 unfortunately. Sucks. Thanks, that means a lot! But May already said she was planning to help me. We were actually going to my house to work on homework, if you wanted to come." Dawn smiled, but it was strained, her eyebrow twitching.

Ah, so May didn't explain to him how she was in Geometry yet, huh? She wondered how she was going to deal with this. She wondered if it would turn into a train wreck. She sincerely hoped it wouldn't.

However, judging by how panicked May was and the fact that May had no knowledge of algebra 2, there was a good chance that things would indeed, turn into a catastrophe.

Either way, in case it did, she had to be there. She decided that she had to make sure May didn't panic and freak out like she usually did. To do damage control, of course.

"Sure, why not? What time were you guys going?" she asked. Ash looked at his watch.

"Well, May said she was going to be in the library. I don't know if she's done yet, but she said she would be there for a while. I was going to go do other homework while I wait for her."

"Oh, cool. Were you planning to go to the library too?" He shook his head.

"Nah, I usually just try to find an empty classroom that's not locked so I can play music. The library is _too_ quiet, and I hate when it's so quiet. I usually fall asleep in libraries," he explained, scratching the back of his head. Although, admittedly, he figured with how tired he was, he would fall asleep regardless at the moment. Dawn nodded, agreeing. "Want to help me find a classroom while we wait for May?" he offered, and she nodded, giggling.

And the search for an empty classroom began.

.

May walked to the classroom, surprised. "Video/photography club. Seems like my type of club!" May said as she grinned so big. Truthfully, she needed a break from algebra and math. She spent so much time reviewing it and attempting to understanding it, that she needed a break. So, she did just that, with looking for another club she could try.

She actually looked to the bulletin board this time, to check the different clubs and extracurricular activities going on today. Hence why she found herself in front of the computer lab. She grinned, actually excited about this club.

May walked into the computer lab, surprised to see two figures on the computer, glued to the screen. She tilted her head, confused.

"Um, hi," she said nervously.

She saw a boy with dark green hair and glasses. She also saw a blond haired boy leaning over the other guys shoulder, watching the screen just as intensely.

"What a lively club," May grumbled sarcastically.

They looked up to her, curiously.

"Hey, you lost or something?" the boy with green hair asked, raising his glasses up the bridge of his nose.

"Depends, is this the video/photography club?" They quirked an eyebrow.

"Why yes, yes it is. You see, we usually don't get many students joining. Sorry about that, my name is Conway, and this is Trip," Conway said. Trip simply raised a hand, waving hello. "Right now, we were just editing some photos for the yearbook."

"Ooh, can I see?" May asked, moving towards them and looking at the computer screen as well.

"So what interest you? Video or photography?" Conway asked, hiding his heated face. May looked at him oddly, wondering why he was acting so weird. She shook this odd feeling off, however, deciding to explain her childhood dream.

"Well, video. I actually like the idea of having my own show, you know? May's expedition, is what I would call it! It would showcase all my great adventures and such, and it would be totally awesome!"

"Uh…huh," Trip trailed off, while Conway merely fixed his glasses again, seemingly out of habit.

"What?" she asked defensively, raising an eyebrow. Trip merely shrugged.

"It's nothing," Conway answered, moving his hands to cover Trips mouth. "Do you have a video camera?" he questioned. She shook her head no.

"Do you have the slightest idea what you would be doing?" Trip asked. She shook her head no once more.

"O… kay," Trip said, in thought. He trailed off and soon sighed. "Listen, maybe-" Conway quickly tried to shut his mouth. Muttering something she could not hear in his ear. She saw Trip roll his eyes, while Conway turned around and smiled creepily at May. May took a few steps back, a shiver running up her spine.

"That's totally okay you have no experience with a camera! We can teach you! Usually, we don't really have much of a budget given to us by the student council, so in the meantime, you can borrow my camera whenever you feel like shooting something. It works photos and videos. I can teach you both, if you like," Conway offered. May instantly brightened, a glimmer in her eye.

"Yeah, that would be so awesome!"

"Other things we do include editing videos with Sony Vegas and working Photoshop with the photos we take. It's really practical to learn, you know," he continued, making May more and more thankful she decided to check it out.

"Now this sounds so cool! I'm so glad I joined!" May gushed.

Even though the two members of this club were a little on the odd side, it still seemed like a pretty sweet club for her. She was told she needed to consider her future all the time, anyways.

Plus, it's not like she wasn't weird either, hah.

She would fit right in with these dorks.

They were all surprised when they heard knocks.

"Wow, we're getting a lot of members today, ey," Trip said, rolling his eyes as he continued to look at the computer screen. Just then, the door opened to reveal a frantic girl making her way into the classroom.

"Ah, sorry I'm late! I hope I didn't miss much!" a voice said, rushing towards the three. May grinned. Conway nearly choked on air and Trip raised an eyebrow.

"Hey, it's you! You were really nice to me before. Serena, right?" she asked. She nodded.

"Yup! May?" she questioned, and May nodded, winking and posing in victory.

"The one and only!"

"Cool, I didn't know you joined this club. I haven't seen you in culinary club," she mentioned. May sheepishly laughed.

"Uh, yeah, I figured I burned down enough kitchens," she said, and Serena laughed.

"It's okay, we all make mistakes," she said, smiling at the girl. May nodded, thinking how she may make a little more than the average person.

Then again, May wasn't exactly average by anyone's standards.

"Hi, welcome to the video and photography club!" Conway said rather shakily. May stared at him, wondering what was wrong with him. Trip shook his head with disappointment.

"Probably just excited to have more members, bonus that you two are girls," Trip explained. He ended up staring at Serena.

"What got you interested in video and photography?" Trip asked.

"Oh, well, I saw some videos online with people making clips for contests online, and I wanted to try it!" Trip nodded.

"Well, this would be the place for it," he said. "Do you have a camera?" he asked. She shook her head no.

"Well, looks like we're going to have to use Conway's," Trip mentioned.

"I'm perfectly fine with that," Conway said, bouncing back up. "We can even make a schedule on when we are going to use it and for what," Conway suggested, already taking out a piece of paper and a pen.

"Here, I can show you guys how to use it," Conway offered. They all nodded, excited.

"First episode of May's Expedition is on the way!"

"I can't wait to try this out," Serena said enthusiastically. "Ah, I need to practice what I'm going to say… and costumes, and hair," Serena began to panic.

"Hey, don't worry about it," May said, winking. "I'm sure you'll be great! I mean, I'm no expert or anything," she began, realizing she was never on TV or anything like that. "But from my experience, I know it's better to just be yourself!" she explained. Serena nodded, grateful.

"You're right. Thanks, May," she said, grinning at her. May grinned back, giving her the peace sign.

"No problem! I mean, you helped me so much in culinary club when I was the worst, it's the least I can do!"

"To new members!" Conway cheered, hoping this meant that the budget given to them would increase.

"Oh, that reminds me!" Serena said, her face brightening. She shuffled through her bag in hopes to find her plastic container filled with all kinds of treats. "I made these in culinary club today!" Serena said, a small blush rising. "I hope you all like them!"

"You're amazing!" Conway gushed. May's stomach growled. She chuckled before reaching for a baked good.

"Oh, this is going to be my favorite club if you keep bringing treats like this!" May said in between bites.

The rest of the club meeting consisted of ice breakers and learning how to use Conway's video camera so they could begin filming.

May was more than excited, finally feeling she found a club where she truly belonged.

.

May tapped her foot, her arms crossed and her expression annoyed.

"Okay, today, I didn't get it wrong. We were going to meet at this time to study. He's late!" May furrowed her eyebrows, frustrated. "What's he doing?" she wondered, off through the halls to look for him. It wasn't until she heard music, that she peeked in a room.

Her annoyance faded for a second, when she saw Ash and Dawn laughing as their heads bounced to the beat of the song.

But it only faded for a second.

"Ahem," she coughed, her arms crossed and her face having the most annoyed expression she could muster.

"You know, I've been waiting for a while now, Ash Ketchum," she said, eyeing him suspiciously. Ash jumped a bit at hearing May's annoyed voice. He scratched the back of his head, looking sheepish.

"Ah, already? Sorry, we lost track of time."

"Uh-huh…" she trailed off, trying to think of something else to say.

"She hates waiting around for people, trust me," Dawn chimed in, helping Ash understand. Ash nodded, agreeing.

"Well, now both of you owe me," May decided, smirking.

"Hey, I wasn't the one who set the time to meet up with you," Dawn argued.

"But you're partly responsible Ash was late," May argued back.

"No way!" May stuck out her tongue in defiance. Dawn shook her head. "We were just doing homework, anyways."

"Uh-huh… sure," May said, and Dawn furrowed her brows, frustrated with her best friend. She knew just what buttons to press, it seemed like.

"Urm, so… are we going?" Ash wondered, looking between the two. Their little argument seized just like that, both nodding eagerly.

.

When they finally arrived at Ash's house, both were curious where he lived. It was a quaint house it looked like, nothing out of the ordinary, but definitely nice.

Both Dawn and May smiled when they were greeted by Ash's mom.

"Why hello there," she said, looking cheery at the both of them. Both girls inwardly grinned at the sight of Ash hugging his mother as they made their way inside.

"Hi, Mrs. Ketchum! It's a pleasure to meet you!"

"I heard you were going to be helping Ash? I sincerely thank you. When I found out he was falling behind in math, I told him his grades better improve or else he can't play sports. His teacher called and said how he's not paying attention in class. It reminds me of all those times I always tell him to change his-"

"Mom," Ash whined, hoping she didn't say anything embarrassing. Delia began to giggle at Ash's red face.

"Oh, it's not like that happens anymore," she reasoned. Ash's face still heated even more, looking over at both Dawn and May, who were giggling amongst themselves.

Yeah, he was super embarrassed now.

"Okay, okay, we have to study!" Ash yelped, hoping to change the subject so they could get to work. Delia nodded, moving toward the kitchen. Ash sighed, relieved. He sat at the dinning room table, bringing his books and bag on said table. Dawn and May did the same.

Dawn bit her lip, hoping May had a plan for tutoring him. She watched as May confidently opened Ash's textbook, looking for the chapter he had to work on.

"So, what exactly do you need help with?" May asked, her eyes locked on the textbook and smirking at the familiar chapter.

"Everything! I didn't pay attention in class. I saw all these equations on the board – they look pretty familiar, but I just don't know what to do with them," Ash explained. May nodded, cracking her knuckles and her neck, and getting to work. She began explaining how to factor quadratic polynomials and its different forms. She also showed him how to identify these forms in more elaborate polynomials that aren't necessarily quadratic.

Yeah, Dawn was surprised too.

When she began explaining algebra 2 concepts to him, Dawn's jaw hung incredibly low, completely flabbergasted at the sight before her.

 _Who was this person?_

This wasn't her ditzy friend who could barely swing a bat or who fell asleep in class.

By the time they were working on actual problems, May watching him do them and correcting him if he forgot something, Dawn smiled, proud of her best friend.

She was happy she didn't have to do damage control after all.

"Okay, now you should be able to do these on your own! Let me know when you're done so I can check them," May said. Ash nodded, beginning to work his homework problems.

She was in awe, wondering how she was able to do this – to know all this!?

She looked to her own homework, deciding to just focus on that.

She would have to ask her later.

May's face brightened.

"Hey, these are right! See? You got it, easy!"

"Thanks, May! I knew I could count on you!" Ash said, truly thankful. May blushed, a bit embarrassed by his gratitude.

"I mean, it's the least I can do, right?" she said, looking confident and smug. Ash nodded, mouthing another relieved thank you.

"Hey, are you two hungry? I can bring some snacks?" Ash asked, getting up to head to the kitchen. May nodded vigorously, never one to turn down free food.

"Yes please! I'm starving." Dawn merely laughed at her friend, agreeing.

When Ash left the kitchen, May turned to her best friend, smirking.

"Okay, now that we're all in the same room, I think it's the perfect time to ask him." She winked at Dawn, and Dawn's face unknowingly began to turn red.

"Ask him what?" she wondered, fear emanating from her tone of voice.

"About the rumors, of course!" May whispered, a wicked giggle forming.

"What rumors?" Ash asked, coming back. May smirked, staring him in the eye. Not before grabbing the unopened bag of potato chips, of course. She began to giggle some more.

"Ash, are you as dense as they say you are?" she asked. Dawn's eyebrow twitched, wondering how May could be so forward. Ash furrowed his eyebrows, not understanding what she meant.

"People think I'm dense?" he asked, confused. She nodded, giggling.

"Obviously. Like, do you even look at girls like that or anything?" May wondered, tilting her head and staring at him head on.

"W-wha?" he wondered, completely surprised. "People question if I like girls?"

"See? Dense! I knew it!" May said, giggling. "You like, barely even look or really talk to girls unless it's as friends, right?"

"Eh?"

"Ash, give me more to go on."

"I'm just wondering where these crazy rumors came from? Of course I like girls."

"But in the relationship type of way?" Dawn wondered curiously. Ash shrugged.

"I mean, obviously. I dated before, you know," Ash explained. Both Dawn and May stared at him incredulously.

"Really? Woah. You'd think we'd know, huh? Wait, so what happened? Who?" May asked like a curious child. Ash leaned back, his face heating because of how flustered they were making him with all these questions.

"It's because it was only a few dates - we were kind of a thing. I mean, I dated other girls besides her, but those were only a few dates too. It's usually because I don't really have time to go on too many dates. Definitely no time for a girlfriend, right now anyways," Ash thought aloud, realizing how he's _already_ struggling to keep up, without a girlfriend. "But I definitely like girls," he explained, scratching the back of his head, wondering why he even _has_ to explain this.

This is the first time he's ever heard of these rumors.

He didn't like them one bit.

"You failed to mention who, though," May reminded. Just like May, getting into the more pressing issues.

"That's because we agreed not to say anything about it or talk about it," Ash said. "Only a few people know about it." Ash shrugged. May's brows furrowed.

"And we can't know?"

"Definitely not," Ash answered.

"Why not?" May pouted. Ash shook his head.

"Secret!" he said, grinning at the two. May frowned.

This was going to kill her. She slumped in her chair, contemplating.

She smirked despite herself. May straightened up. She loved a good mystery, though.

"Thank you for telling us what you can," Dawn said, a small smile creeping up. May nodded.

"Yeah, that means a lot." Ash grinned at their words.

"Still going to find out who," May mumbled under her breath. The other two did not hear her.

"Of course! You two are really great friends now," this was the first time he said that, and the first time he really realized it and let that sink in. It was no surprise, he was spending more time with them than all his other friends now. They quickly became close friends for him.

They all smiled, grateful for this newfound friendship.

.

As they all took a break from homework and studying, Ash thought for a moment, staring at Dawn with curious eyes. His brows furrowed in concentration, trying to put her face and name to a previous memory.

"I swear I've seen you before! Like, was it last year, or middle school? Elementary school? Summer camp?" Ash thought, and Dawn giggled, sticking out her tongue.

"No need to worry! I'm not telling anything, until you remember!" she said, before winking.

"Oooh, or if you let us know who you dated in the past," May suggested, winking. She paused for moment.

"Hey, wait a minute… you haven't even told me!" Dawn smirked.

"I'll tell you after. You like mysteries after all, right?" Dawn said, sticking her tongue out at the both of them. Both Ash and May crossed their arms, their faces scrunching up in frustration.

Ash grumbled, "But I'd wish you just tell me already." He thought, still struggling to figure it out.

"Well, there's no time for worrying about that right now! You got a quiz to ace!" May barked, trying to get them all on track for the goal at hand: bring Ash's grades up!

Ash nodded, focusing back to his textbook and ready to work the heck out of these problems.

.

 _AN:_ Sorry, for the long wait. Honestly, I had no motivation to complete this chapter. Welp, there we go! Hope this sufficed. At this point I'm going to start adding more… bizarre characters and a little more interesting scenarios and scenes… xD Either way, hope you guys like the little nods I gave to different pairings (what I mean when I say multiple pairings, heh). If there are certain characters you want to interact or see more of, please let me know now. I'll most likely do it, heh. Also, I promise there will be more basketball training next chapter, haha. Please review and let me know what you think of this chapter! Also, please vote in the poll in my profile, I made a new one since I added more options of what to work on next! Till next time!


	6. Collection

_AN:_ Full disclosure: I'm going to be completely honest and say that I base what pairings I write in the chapter based on what I'm hearing/ what the majority of what you readers want (so please don't feel bad for telling me which ships you want, it actually helps me come to a decision. Don't think it's a bother, it's actually nice knowing people care enough about that tbh)… xD Cause otherwise, it most likely would be strictly friendship between everyone (I mean, I guess you can argue that it's all just friendship now - it pretty much all is lmao), but yeah… so forewarned, there will be a lot of advance (a little bit of pearl and contest too) and another funny ship. xD

.

 _Count:_ 5342

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Chapter 6:  
 _Collection_

.

Ash grinned.

"You ready?" he asked, feeling better than ever.

May groaned.

"No…" she grumbled.

"Come on, May, it's a great day!" Ash said, beginning to stretch his arms.

"Oh _sure._ Hey, aren't you supposed to be the sleepy one?" May asked, annoyed and cranky. Ash continued to grin.

"Yeah, well, I have you to thank for that!" Ash said, his fingers meeting his toes as he took a deep breath of the crisp air. Early morning runs were never May's strong suit, however, today especially was not a good day for her. "If it wasn't for you, I wouldn't be able to go to sleep early, trying to finish impossible homework. I think I even aced my last quiz! Thanks again, May!' Ash said gratefully, reaching his arms in the air and stretching his triceps.

"You're welcome," May smiled back, grateful for that at least. At least she knew it was kind of working. He definitely seemed more confident about algebra.

"Great! Now let's get to running, we still have to get you on the girls' basketball team, and you still need a lot of work!" Ash called, starting to run in place before taking off, feeling energized and ready to take on the world.

"Hey, wait up!" May called out groggily, trying to keep up. May was just trying to not get crushed by the world, tired and struggling.

"You better get into the swing of things quick! We need to make up for all the lost time we missed last week!" Ash said, grinning wildly. "Let's just say there are going to be a lot of burpees in today's practice."

May inwardly groaned, wondering if he was intentionally trying to torture her.

The jerk.

Someone just kill her now before Ash does in practice.

.

"Come on, May! Match my speed!" Ash called as they continued to pass the ball back and forth, moving sideways across the basketball court.

"I'm trying to keep up!"

"You're going to have to keep up during actual practice, when you make the team! Come on, May, let's go!" Ash encouraged, continuing to pass the ball with ease. May nodded, panting as she tried to increase her speed.

"You need to learn how to pass well if you're going to make it to the team," he said. May nodded, passing the basketball back to him and heading to the other side of the court once more.

Today's practice consisted of a number of passing and shooting drills. She needed to get better if she wanted to get the position she wanted.

After practice, Ash stretched, feeling tired himself. Still, he smiled at May, proud of her hard work.

"Wow, great job, May!" Ash complimented.

May fell to the grass, exhausted.

"That the hardest I've ever worked," she said in between heaves.

"I can tell! Maybe that break did you good," Ash thought, walking over to her and handing her a water bottle. May smiled.

"Thanks," she said, before taking it and chugging it down.

She was getting through practice surprisingly fine.

It was the rest of the week that would be kicking her butt.

.

It was a new day, and May was tired.

"Hey, pay attention," Drew urged, eyeing her sternly.

May stared at Drew with a sneer, really dissatisfied in him telling her what to do, because _no one tells her what to do._

 _Especially Drew._

"You're the one who needs to learn this stuff, not me." Drew shrugged, and May groaned, banging her head against the table. She hated when he was right. It was just so hard to focus anymore. She shook her head however, determination in her eyes once more.

"Okay, I will not give up! But still, this chapter is _really_ boring." Drew rolled his eyes, giving a small laugh.

"You're telling me. I almost pulled a Ketchum," Drew said in thought, making May raise an eyebrow. "Oh, it's nothing," Drew said, figuring she wouldn't know what he was talking about. May let it go, since she did not need Drew to know about her lessons from Ash, or even suspect it. But still, his words made her wonder.

"Okay, so if I need to find what the function of this is, I just do this," she paused to concentrate on the problem, using arrows to help her figure out what she was doing. She looked at Drew. "Right?" Drew shook his head.

"No, you actually just have to do this," he started, writing the correct way to finding the function. "And what you're actually doing here is finding the domain of the function."

"This seems like, way too advance for me."

"Don't we all know it." May glared at him, while Drew gave a soft chuckle. May paused for a bit, her eyes averted as she looked down to her lap.

May grew frustrated, hating this. Absolutely _hating_ this. How could she even think this was a good idea?

Sure, she was learning algebra 2, but at what cost?

Especially when he ends up looking at her and she just focuses in on the pages of the book, trying not to let him know that she knew he was looking at her.

He must have been getting a good laugh, she figured.

It gets super awkward. Like, _super_ awkward.

She could not handle awkward, _at all._

Sure, she was usually an awkward and quirky person herself half of the time – correction, all the time.

But there's no way she can be weird like this with _Drew_ of all people.

She absolutely refused to be, not with him. Not after the fact she had declared Drew as her biggest rival ever.

 _"I...I have to find another way to learn this stuff. This is becoming really embarrassing, these library days with Drew,"_ May thought. She kept thinking about other problems that could arise. She started thinking that maybe finding a better tutor for Ash would help him in the long run. When Ash asked May something she didn't know, sometimes, she had to make stuff up, and she figured that wouldn't be the best. She never knew what Ash wouldn't understand, so if she didn't get it completely, the only one who would suffer would be Ash.

She frowned, knowing there had to be a better way to go about this.

Asking Drew would be completely out of the question. She tapped on the algebra textbook, ideas beginning to formulate.

"May," Drew caught her attention. May shook out of her stupor, sheepishly chuckling.

"Right... right," May groaned, continuing to learn all about even more functions and other math equations she wasn't planning to learn until later in life (if ever, hah).

Still, she had to learn it. For now at least.

She focused, continuing to take in as much information as possible.

.

When May finished studying at the library, she staggered all the way to video / photography club. She was too tired from learning algebra 2 to be excited for the club.

She could see why Ash fell asleep in his class so easily.

She rubbed her eyes, making her way in, only to see Trip and Conway already there, on the computer once more – like always.

"Oh, you're back?" Conway wondered, fixing his glasses. She could see the glare from the computer screen, making his face even creepier than before. She shivered, finally awake.

"Yeah, I'm back. Hey, why do you guys always have the lights off?" she wondered before switching them on. Conway hissed as though he was actually a vampire, while Trip rolled his eyes by the dramatics.

"Yeah, it's easier to focus."

"It's easier for me to fall asleep," May corrected, giving a yawn for good measure. "So, what are you guys up to? Still working on the yearbook?" she asked. They both nodded.

"Hey, can I help?" she asked excitedly, walking towards the boys. The boys nodded.

"I thought you wanted to film?" Trip thought, raising an eyebrow.

"I'm going to have to learn how to edit videos and photos sooner or later. Plus, schedule much? I thought Serena was going to use it today?" May wondered.

"Well, as you can see, she is not here, so you could-" Just then, as if on cue, Serena ran in.

"Hi, sorry about being late! Culinary club always runs late. Especially when I'm not finished making treats! I hope you guys like these," Serena said in between huffs, opening a plastic container filled with different pastries.

May's face instantly lit up, a deep blush rising at the kind gesture.

"This is my favorite part of the day!" she gushed, immediately taking one before the boys had the chance.

"You were going to use the video camera today?" Trip asked. Serena placed the plastic container on a table, while she went to take the camera from Trip.

"Yeah! And May, would you be able to help me?" she asked, and May nodded.

"Sure thing!" May agreed.

Serena smiled, excited to start making her contest entry.

.

While May was going to her club, Ash and Dawn decided to do their homework in a classroom once more.

"Hey, race you to the room," Ash said before running off.

"Hey, no fair!" Dawn called, before running after him.

Ash had obviously won.

"You cheated, though. So it wasn't much of a win," Dawn said in between breaths. Ash laughed, soon taking his tongue out.

"Nah, I still won fair and square. I'm the fastest still, remember?" Ash reminded, and Dawn rolled her eyes, crossing her arms as they walked into the empty classroom.

They both found their seats from last time, before Ash scrolled through his music.

"Hey, why don't you pick out some music this time?" Ash asked, before settling down and figuring out what he had to do for his classes. Dawn frowned, feeling the very real social anxiety that comes along with picking music.

"Hmm," she said in thought, before scrolling through her playlist. "Well, what kind of music do you like?" she asked, biting her lip a little. Ash shrugged.

"Anything is fine with me," Ash said. And Dawn gulped, knowing that when someone said anything, they don't really mean anything. At least, that was how she felt. Dawn paused thinking for a bit before deciding to play a particular song – one she thought that might be familiar to him. Ash grinned.

"Hey, is this a new song?" he asked, before Dawn pouted. She was hoping this would surge his memory, but she guessed not. She sighed, shaking her head.

"Nope! Actually, a pretty old one now," she explained, before deciding to just let it go and focus on what she had to do.

When she took out her agenda in her bag, she looked through her homework. Ash couldn't help but notice, his eyes in awe at her neat notes.

"How do you manage to do that?" Ash wondered, completely shocked. Dawn shrugged, a small smile on her face.

"I just write down any homework I have. No big deal," she said, before looking at her first classes homework. She grabbed her folders and began writing.

Ash frowned. "I need to get organized or something. I have to figure out when I'm going to do anything. I had to get reminded today that I have a big group project I need to work on. I haven't even talked to my group partners about it," Ash said, frowning.

"No need to worry, you got this. There's still time, right?" Dawn tried to reassure. Ash nodded, figuring he could start on his part at the very least.

"Yeah, you're right. Can you help me?" he asked. Dawn nodded.

"Yeah, of course!"

"Thanks, Dawn," Ash said, before looking through his history textbook. He hasn't even gotten a hold of his group mates. He shrugged, watching Dawn work, and deciding it was a good a time as any to start working.

It was a good 30 minutes before Dawn received a call.

"Hold on, Ash. I need to take this – my mom," she explained, before she answered her phone and greeted her mother. Ash could see her face fall as she nodded as she agreed with something her mom (he figured it was out of habit, seeing as her mom couldn't see her nod her head).

"Alright, bye mom," Dawn said before hanging up her phone and turning to Ash.

"What's up?" he asked curiously.

"Nothing, I just have to leave early. My mom needs me for some errands. Hey, can you tell May my mom was calling for me and I had to leave early?" Dawn asked as she began packing her bag.

"Yeah, definitely," Ash said, before continuing to finish his homework.

.

"May, are you alright?" Ash asked, a frown etched on his face as he continued to pack up his bag. May sulked, nodding.

"Yeah, yeah," she grumbled crankily.

"You're starting to act like me when I get no sleep," Ash laughed.

"Not that. I get plenty of sleep. Just been studying more," May admitted. Ash smiled, chuckling more.

"That's great! If you're as good in your other classes as you are in math, I'm sure you don't need to study all that much," he complimented. May grinned, no one ever complimenting her intelligence like that. She scratched her cheek, wanting to literally pat herself on the back for a job well done. However, a part of her felt bad, knowing that deep down, she wasn't the best when it came to her studies.

Still, it was nice having one person think so – albeit probably not for long if she can't keep this up.

"Wow, thanks, Ash." Ash nodded, his backpack swung over his shoulder before he motioned that he was ready to leave.

"Hey, so are we going to your house this time to study?" Ash asked. May nodded enthusiastically, excited to show what she learned – well, what Ash is going to learn. May stopped, however, looking around the empty classroom.

"Hey, where's Dawn?" she asked, wondering where she had run off to.

"She had to leave early. She told me to tell you, that her mom needed her," Ash explained. May nodded in understanding, knowing that happened a lot, so she wasn't too concerned.

Time for round two of tutoring!

.

"Okay, so, basically, this is how you do this problem." May made sure to show him how the example problem was done with great ease.

"Aah, okay. Yeah, I've actually paid attention in class. I get the rules of figuring out the difference between functions… and those that aren't. The only thing I'm having questions about is why. Well, I'm just having a bit of trouble with the math part of it, like figuring out the stuff with the domain. I get it when you graph it, but after, it's weird for me," he said, staring at his book and eyeing the problem with frustration as he continued to try to solve it. He scratched his head, frustrated.

"Oh, I think I know this. If I remember correctly, it's..." May trailed off, too focused on the problem to finish her statement as her pencil raced across the paper. She handed it back to Ash so he could look it over and figure out what she did. His eyes brightened.

"Aah, cool!"

It was 45 minutes into studying, and Ash looked over to May pleadingly, in desperate need of a potty break.

"Hey, May? Where's your bathroom?"

"Go down the hallway, third door on your left," May said. Ash nodded, walking through her house. It was rather big, very nice. It _seemed_ like no one besides them was home besides –

"Hey, are you May's boyfriend?" a small kid with glasses asked.

"What? No, we're just friends. She's helping me with math," Ash answered. He raised a brow at the little kid. The boy in question looked on in disbelief.

" _May_ helping with _math?_ May? Hah! That's funny," he said, fixing his glasses as he continued to chuckle.

"It's true, she is," Ash defended, eyeing the boy suspiciously. "She's really smart. Who are you anyways?"

"You must not be the sharpest tool in the shed either if you think that," Max teased, making Ash glare. "And the dork with the giant pokemon collection? Please! Oh? You didn't know? Check it out for yourself," he said, opening the door opposite of the bathroom, and revealing a kind of clean, kind of messy room. And the little boy was right. Ash's eyes widened when he saw a mass of Eeveelutions plushies on the bed. Max walked in, ushering Ash to go in too. Ash took a few steps inside, still in awe at the giant pokemon collection.

"That's my dorky sister, May's room. I'm Max by the way," he said, fixing his glasses some more with an evil smirk on his face. Embarrass older sister? Check. He giggled to himself, knowing the rule that little siblings had to embarrass their older siblings in front of their friends was the number one rule. He was doing a darn good job, if he did say so himself.

Ash looked around the room in disbelief. "Woah," he whispered, completely shocked. Max stared next to him, not shocked, but pleased with himself, patting himself on the back at a job well done.

"Max!?" May scolded, running through the hall. She quickly grabbed his ear, her eyebrow twitching and her eyes glaring daggers his way.

"Ouch, ouch, ouch," Max whined.

"May, you like Pokémon?" Ash asked excitedly. May let go of Max's ear, flustered as she turned her head the other way, her cheeks darkening in embarrassment.

"Ummm, I kind of do, a little, maybe?" May was clearly embarrassed, knowing that it was not all that cool to be such a big Pokémon fan during these times. Only Dawn knew this (Dawn having a piplup plush herself, mind you). She cringed a bit, Ash seeing her Pokémon collection _not_ in today's plans.

"I love Pokémon too!" Ash confessed, grabbing her stuffed eevee and touching its soft ears.

"R-really?" she asked, her eyes wide at the revelation. Ash vigorously nodded.

"I love everything Pokémon," he admitted. "I actually have a stuffed pikachu. I had it since I was ten," he said, clearly enjoying her plush eevee, along with her little torchic. May stopped for a moment to completely process his words, before she grinned.

"Wow, Ash, you're such a _nerd_!" May teased, giggling. Ash furrowed his brows, clearly annoyed at how hypocritical she was being.

"I'm not the one with the stuffed eevees and torchic on my bed right now," Ash commented. "Anyways, Pokémon is super cool. Like _super_ cool! Honestly, it is nerdy now, but just you wait, one day, everyone is going to love it again. I don't get why anyone would stop," Ash predicted.

May scoffed, "Yeah right. You'll always be a nerd in my eyes, Ash Ketchum."

"If I am, then you are too, May Maple." They both laughed, May rolling her eye.

"Did you get the new Sun and Moon games? I have Moon!"

"As if I have time to play them. But yeah, I obviously do – I have Sun. I just haven't played yet. I'm waiting till break to do that," Ash said, already knowing she was planning to gasp in utter disbelief. And that, she did.

"Ash Ketchum, first thing you're doing when break happens is playing your Sun game!"

"Yeah, Mom," he teased. Both laughed, continuing to talk on the floor as May continued to share her various Pokémon games, cards, and plush.

"Hey! I actually have Pokémon plushes and games too," Max interrupted, wanting to be included – especially since he loved Pokémon just as much as them.

"Then bring them, I want to see!" Ash said, while May just rolled her eyes.

"Excuse my brother," May said, hoping he wouldn't be too worried about dealing with a little kid like Max – especially after he completely embarrassed her.

"Haha, he's cool," Ash said, instead following Max so he could show him his collection of ralts, slakoth, and mudkip plushies. May glared at her brother, before getting over it and continuing to explain why Ash needed to obviously play the new Sun and Moon games.

Anything about functions or quadratic formulas was long forgotten.

.

May looked fascinated, hanging onto every word Conway said as he explained to her how to use the camera… _again._

"You understand?" Conway asked, fixing his glasses. May nodded vigorously.

"How many times are you going to explain it to her?" Trip grumbled to himself.

"Ahem," May coughed loudly, motioning for Trip to shut his trap. "Actually, yes! I can't wait to start filming about my adventures!" May started, grabbing the camera from Conway and trying it out herself. Her tongue stuck out, trying to focus and remember exactly what she needed to do in order to work it. "Okay, so this is to turn on the flash, this is to adjust brightness, right? And this button will zoom in and out. Okay, I think I got it!" May exclaimed, holding it up to her eye before she pressed play and began filming.

"Today, on May's expedition, we get to take a better look at the video/ photography club and their inner workings! I'm here now with the president of said club, Conway!" Conway fixed his glasses out of habit, turning away from the camera.

"I-I'm not one for the spotlight," Conway tried to say, hiding his deep, embarrassed blush.

"Oh, come on! It's going to get us a lot more people to join! Imagine if we had a cool commercial that we can show everyone, or put on the school website!" May reasoned, continuing to film him.

"W-what?" Conway stammered, even more nervous.

"You just have to get in your element! Okay, tell me a little about yourself!" May tried, hoping this interview style filming would work. Conway fixed his glasses for the hundredth time it felt like (more so now out of uneasiness), feeling extra nervous. May sulked, wondering why he was being so shy. He was definitely not like this before.

"Um, okay, tell me about... the quadratic formula, or... Oh, tell me about solving for a function and or other algebra stuff!" May said, laughing at herself at the ridiculous thing. All she could really think about was math after her study session with Drew, so it was the first thing to come to mind.

Conway, surprisingly, wasn't so shy anymore, fixing his glasses he asked her what question. She shrugged, handing him a paper with a problem. Conway immediately began to explain said problem in full detail, even going to the dry erase board and writing the problem May suggested.

"What the... woah, you're like, an encyclopedia or something," May complimented, continuing to film him completing the problem with the camera. She was in complete shock. Conway smirked, fixing his glasses once more with confidence this time.

"Well, when you're in AP Calculus, this stuff gets ingrained in your head. Geometry, algebra, and trigonometry are a piece of cake for someone like me." May stood there, still completely out of it as she tuned Conway out and started to think of a plan.

Conway was a junior, yet he was in AP Calculus, so he had to be a genius (in May's eyes). It was the perfect opportunity to get Conway to help tutor Ash without Ash being none the wiser. She knew it would be difficult to keep up trying to tutor him by going to Drew all the time. Plus, she couldn't just ask Drew to help tutor Ash, that would defeat the whole purpose. It felt like a light bulb went off in her head.

"I just need to find a way to get Conway to agree," May thought, feeling as though Conway wouldn't be easy to sway.

"I guess it wouldn't hurt to ask him. I can be very persuasive at times," May said to herself, thinking back to how she was able to persuade Ash to help her. But then again, not everyone was like Ash. She shrugged regardless, hoping to ask him after film club was over.

She decided to just keep practicing with the video camera, knowing she needed all the training she could get.

.

"May, are you done using the camera?" Serena asked, smiling politely. May grinned, nodding.

"Yeah, all yours! Only, I just need to find a way to save what I recorded. It will actually be very helpful!" May exclaimed, not letting this opportunity of having Conway explain that algebra concept so easily pass her by. She was sure it would definitely come in handy.

"I can help with that," Trip said, moving away from his desk for a moment to retrieve the camera and help her upload the video on the computer, so she could email it for herself.

"Don't you have a flash drive or something?" Trip asked, rolling his eyes at her incompetence. Seriously, who uses email like that anymore?

May looked flustered, retorting with a shaky, "I lose them too often," before going back to typing in her email address. She pouted when she realized the size of the file was too big to send.

"What good is email if they can't even send big files?" May crossed her arms, annoyed. Trip shook his head.

"Here, use this flashback for the time being. But I expect it back." May's eyes grew watery, completely taken back by his surprising generosity. She didn't think Trip liked her much with how sarcastic and I-don't-care personality he gives off.

"Wow! Thanks, Trip!" she said, happy that she finally had something to help.

"I expect it back asap, and I expect you _not_ to lose it," he warned. May nodded eagerly, surprised with Trip yet again.

May then walked to Conway.

"Hey, Conway!" May greeted, before Conway turned to her and fixed his glasses.

"Yes?"

"Well, I was wondering, I have this friend that needs a lot of help in algebra 2, and-"

"Let me stop you right there," he interrupted. "I only accept cash payments for tutoring. I have a list of price ranges, if you want help. Sorry, my genius comes at a cost," Conway said, holding up his list of different rates depending on how much was paid upfront, how many hours was needed, and what class it was. Conway was no joke – he knew how to manage his time and get paid. May yelped, exceptionally sad by this fact.

"You gotta be kidding me!" May sulked, feeling down.

"Hey, gotta pay for new equipment somehow," Conway said, giving her a smirk. He shrugged.

"But, I don't get any money!" May exclaimed.

"Well, sorry. I mean, I'd help you, but yeah, doesn't come cheap." She sighed, wondering what she was going to do.

She was going to be stuck with Drew for all of eternity it looked like!

Plus, May knew Ash couldn't get everything with just her mediocre help. She frowned.

"There has to be something I can do to convince him," May whispered to herself.

"May!" a voice came from the other side of the room. Dawn walked in, waving at her friend.

"Oh, hey," May greeted, a soft smile forming.

"So this is the club you're in - the one you won't stop talking about?" Dawn asked, looking around. Dawn raised an eyebrow - didn't seem like much of a club.

"Yeah, let me introduce you! Over there is Trip, the vice president, that is Serena, a newbie like me, and that is Conway, the club president!" May introduced. Dawn smiled, before taking a step back when she looked at the gleam in Conway's glasses.

It kind of creeped her out the way he looked at her. A shiver crawled up her spine.

"Nice... to meet... all of you," Dawn said awkwardly, feeling Conway's eyes on her. She quickly turned away, knowing he was kind of a creep, especially now.

"Nice to meet you too!" May sighed, before she noticed Conway hiding his deep blush, not taking his eyes off of Dawn.

May looked between Conway and Dawn, not sure if she was reading the signs right.

It took her a moment to put two and two together.

"Oh, my goodness, it's like I've been given a miracle right in the palm of my hand!" May said, feeling like she should just get down on her knees and start praying then and there. She felt like she won the lottery.

"Ummmm, May? I'm going to wait outside for you, I'll see you later! Nice... um, meeting all of you..." Dawn said awkwardly before rushing out of the room as fast as she could, trying to rub away the goosebumps that arose.

Seriously, Conway could be such a _creep_ at times.

When she was out of sight, Conway still held a blush, his mouth agape and his glasses out of place (nearly falling off even), yet he made no move to fix them as he continued to stare at the door Dawn walked out of.

"That's _your_ friend?" Conway asked, completely stunned. May smirked knowingly.

"Yes she is, my BEST friend, actually," she stated proudly. Conway finally got out of his stupor to fix his glasses, his face still beet red.

"H-hey, you know, you should tell your friend to stop by more often... I mean, I was just thinking, she would be perfect to include for the yearbook," Conway tried to say. May raised an eyebrow.

"How about I introduce you for real..." May started. "At a price, of course! The price of tutoring lessons," May began, a small smirk on her face.

Conway fixed his glasses, coming out of his euphoric state and ready to negotiate.

"Just an introduction? No way. I'd only help with tutoring, besides money, are for dates," Conway said. "If I could go on a few dates with _her,_ then I would tutor your friend the whole year if need be..." May's face fell. No way Dawn would go for that.

"What?"

"You heard me: only way."

"B-but!" May stammered, trying to figure out a way to get around this. She sighed.

"Okay, okay, what if I say I can most likely get you _one_ date?"

"Five," he argued.

"One."

"Three."

"One."

"Two."

"One! And I pick the circumstances, as in location and how long," May reasoned. Conway thought for a moment, before figuring that anything with Dawn was actually better than nothing at all.

"Okay, fine, you have a deal. Only if you manage to pull this off, though," Conway said, a smile creeping up to his face. May jumped, her eyes glazed with optimism.

Her plan was going just perfectly! She may actually pull this off!

She smirked.

"Hook, line, and sinker!"

Her plan seemed to be working out just swimmingly.

Only one problem: she had to find a way to convince Dawn of this oh so "perfect" plan.

She bit her lip, hoping her friend would agree.

She gulped, knowing this might not work out so perfectly after all.

.

Dawn raised an eyebrow, wondering what May was doing.

"Um, May? Why are you in that club, by the way?"

"Because it's really cool!" May told her excitedly. "I'm learning a lot about camera work and stuff. It's really cool! I'm going to be like, a TV star, you wait and see!" May winked, and Dawn nodded, happy for her friend's passion.

Dawn stopped, feeling an odd aura, like someone was watching her.

It felt creepy.

 _Really creepy._

She turned and shivered, when she felt Conway's eyes on her, who was trying to hide his blush. He was by the door of the computer lab, watching longingly.

She could barely see it, but he mouthed a whispered, "goodbye."

Another shiver, for the hundredth time it felt like, ran up her spine.

Yeah, he was _really_ creepy.

May's face light up, feeling this was her chance.

She had an evil idea formulating, excited for what was to come.

.

 _AN:_ There we go. I delivered on the next chapter hehe. Loooool, this is where all the insanity and chaos ensues for everyone (you all already got some of it in this chapter)! xD Please tell me what you think of this chapter, please! Would love feedback! ^_^

What is to come (because I'm super excited to write with how funny it is in my head): **Chapter 7 – Chance** ; continuation to this, introduction to Barry, 60% more Paul, and more creepy Conway xD Someone asked for some Gary and Misty interaction so I'll add a little bit of that (and maybe some other crazy stuff haha).


	7. Chance

_AN:_ This one was SO MUCH FUN TO WRITE! I hope you guys enjoy this as much as I enjoyed writing it! ^_^ Sorry this chapter took so long haha. However, I bring you a long chapter to compensate for the wait (although I apologize in advance, my descriptions aren't on point at all. I am pretty rusty after a long absence of writing)! However, this will be my longest chapter yet for this story! Cheers! ^^ Sorry y'all, **I totally had to reupload this because I completely changed the Serena/Gary scene (because I love subtlety and so thought this would be funnier/better).** I hope you enjoy!

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Chapter 7:  
 _Chance_

.

"NO, NO, NO, NO, **_NO!_** " May tried to count how many times Dawn said "NO," but she lost count after thirty. May frowned, completely dejected, her head hanging low and her hair not as voluminous as it usually is. She sighed hopelessly, knowing she had to get through to her friend somehow.

"Please?" May begged, _pleaded_ once more, her hands clasped together, praying for Dawn to budge an inch. Dawn sighed as well, ready to give her answer for the fiftieth time.

"No way! He is a creep! I-I can't do that!"

"Come on! He's… a sweet guy," May tried to say, albeit hesitantly. Dawn rolled her eyes, her arms crossed while she vigorously shook her head.

"He takes pictures of all the cheerleaders!" Dawn retorted.

"For the year book!" May argued back.

"Bottom-line: he's a creep! Have you noticed the way he looks at me?" Dawn asked, her hands over her arms and trying to stop the goosebumps from forming. She just got such an odd vibe when near Conway, he makes her quiver. There was no way she could be alone with him for even a _minute._ May looked away, her eyes averted to the white ceiling.

"No, of course not," she lied, hoping to somehow overlook Conway's odd behavior. Yes, he can be weird at times, but from what she gathered, he was still hard working and knowledgeable. He had a pretty cool personality from what she could see at video club. Dawn shook her head no again. May whimpered, knowing she desperately needed Dawn for her plan to work.

"Come on! I will totally owe you one! For real! You know what that means!" Yes, Dawn knew. She even paused for a second, her eyes sparkling for a second, knowing an I owe you, especially one of this magnitude, would mean Dawn would get to ask/ tell May to do anything she needed, no questions asked.

It was tempting. Very tempting. Extremely tempting, actually.

"Hmm." Dawn's hand rested over her chin in a thoughtful pose and wondering if it was worth it…

But no amount of "I owe you ones" would make Dawn date _that_ guy.

"Sorry, May, but he's a total creep!" Dawn shivered at the very thought. "I have to go now, I can't be late to practice," Dawn said, closing her locker and waving goodbye.

May nearly cried, sulking at Dawn's reluctance. She could tell, that she almost had her, too!

She needed just one more little push.

"I… I can't give up just yet!" May cried, her fist clenched and her eyes still burning with determination.

"That's right, it's not over yet! I know Dawn will give in… eventually," May gulped, before running to the gymnasium, ready to do whatever was necessary to get Dawn to help her out.

.

May sat in the gymnasium, watching her friend practice her routine. She smiled, happy for Dawn who was doing so well - it seemed like this was her niche. The cheerleaders were on the sidelines, practicing their cheers while some of the boys were coming out into the gymnasium, ready to get started on their practice.

Now, something was _very_ peculiar to May. May eyed Dawn, wondering what was the deal with her. She remembered stopping by at times, seeing Dawn's practice when she wasn't so busy. Dawn would _always_ focus, giving it her absolute all, her attention completely on her routine.

But today was different.

Dawn was distracted.

She continued to watch Dawn, noticing her act differently as soon as more of the boys stepped out of the boy's locker room, said boys starting to stretch.

It was her best friend, so of course she recognized the signs. At least she thought she did. Dawn avoided looking at the boys at all cost. If she did take a glance over to the boys, she would quickly look away, her face heated. It was like a battle on whether to turn her head to see the boys; a battle Dawn was losing.

"Hmm..." The gears in May's head were turning, inquiring why Dawn was acting so strange.

May paused that train of thought, however, her eyes widening when she realized Drew and Ash were walking into the gym... _together._

"Oh no," May whispered to herself, sneaking out the gymnasium before either of them noticed her.

May looked back, watching Dawn's odd behavior continue.

May shrugged, then nodded to herself.

"I'll ask her about it later," she decided, her eyes meeting with Drew's for a second before she left the gym.

.

Dawn took a big bite of her sandwich, stuffing her face for once.

May scrunched her nose with impatience. Wondering why Dawn had to stuff her face the _exact_ moment she asked her about why she was being odd at practice yesterday.

Dawn swallowed, before she coughed, trying to stall as much as possible. It was certainly killing May, who just wanted to know as soon as possible.

"Well?" May questioned.

"Okay, the thing is... I might have a small crush on someone," Dawn finally admitted. May nearly spit out her milk, completely flabbergasted.

"WHAT?" This was news to her. May's fist slammed against the table, completely unaware of this.

"Well he's kind of cute..." Dawn brushed through her long blue hair, her pale cheeks now a light shade of pink.

 _"WHAT?"_ May repeated. Dawn blushed at May's outburst, twiddling her fingers together. Luckily, the cafeteria is always loud to drown out May's shouts.

"Okay, honestly, it's not really a crush. I think he likes me, but I have no idea. You know that feeling when you hear someone likes you, and you, I don't know, start to think that you might like them back? I guess I'm feeling that way. I don't know, it gets super awkward because I don't know if the rumors are true or not. If they are, let me just tell you, that will be a massive ego boost knowing someone like _him_ would like me."

"Who?" May continued to pester.

Dawn sighed, ready to explain.

.

It was a regular practice for Dawn. However, she stopped when she saw the other girls lose focus. Her nose scrunched up, wondering whose idea it was to have practice at the same time the boys were practicing. She ended up turning regardless, wondering what they were looking at. It was then, that she watched Ash do a layup, and smiled for her friend. She frowned, however, knowing it might never happen with him. Every girl in the school knew that Ash was oblivious. She knew that wasn't entirely the case, but she knew how busy he was. It would be next to impossible… if she did sort of have feelings for him, anyways, which she of course denies. She took one last glance at Ash, before sighing and looking over to Paul who was on the opposing team in this mock basketball game. He was so quiet, so mysterious - always with a stoic face. She was curious as to why.

She looked over though, curiously. She had seen him a few times down the hall, and sometimes, he'd even make eye contact with her. Even now, he must have felt her eyes on him, for he stared right at her. Dawn blushed, looking away from his intense stare. Before she had time to muster up the courage, she heard hands slapping together.

"Wow, Paul's 3 point shots are incredible!" a cheerleader squealed. The group of cheerleaders giggled when they saw the boys. Dawn was looking over at the game for a bit too, before she jumped at the man standing next to her, his arms crossed and a sly smirk on his face.

"Barry?" Dawn questioned, wondering why so many people were trying to sneak up on her all of a sudden.

"The one and only," Barry said. He was going to continue, until a few of the cheerleaders giggled.

"Hey, Dawn, was Paul checking you out?" a girl named Lyra said. Dawn blushed, embarrassed at the thought.

"You know he's not one to check people out, right? You're special," another said.

"W-what? No way!" Dawn denied, her cheeks so incredibly red now. She was a catch, of course. There were actually quite a few guys who would ask her out, but never had someone as popular as Paul, check her out (Okay, besides Gary, but Gary flirts with everyone). Or so they said. He was probably just looking at something else for all she knew.

It was Paul, after all.

"But he was staring at you so passionately! He never stares at anyone else like that!" Dawn's blush deepened.

"You are all reading too much into this!" Dawn said nervously, trying to laugh off their schoolgirl gossip.

"I agree with you. He's not into you," Barry said a matter of fact-ly, his eyes glazed with smugness.

"I wasn't… wait, what makes you think that?" Dawn asked, quirking an eyebrow. It was one thing for her to think Paul wouldn't check her out, but it's another thing for this guy to say so. Barry was certainly a character. He was part of the cheerleading team, adding more flare and allure to the squad than any of the girls could.

"He's gay, obviously." Barry smirked, giving Dawn the side-eye, his arms remained crossed. Dawn scoffed. Barry fixed his cheerleading pants and shirt, ready to give it his all.

"What? No, I don't think so."

"Mmmhmm. He is."

"What makes you think that?" Dawn asked, her hands now on her hips as she questioned the boy.

"He's never had a girlfriend."

"That doesn''t mean anything. He's quiet, he can just be shy," Dawn tried to reason. Barry shook his head.

"Every girl that tried to ask him out gets rejected."

"Well, I've never asked him out."

"And you think you can get him?"

"I bet I can show you that he is definitely into girls." The two glared at each other, their fist clenched and their eyes throwing daggers.

.

May sighed after Dawn finished telling her tale, shaking her head. What was the deal with so many weird bets all of a sudden?

"One look?" Dawn blushed again. May took a sip of her milk.

"No! It's not even like that!" she defended, taking a step back. May nodded. "Okay, it wasn't my best moment." She had turned into May for a moment. "But I can't just back down now. It was really stupid, I admit." Dawn shrugged. May thought about it for a moment. "I don't even know when I'll find the time to even try. I have to help come up with new cheers and get this project done." Dawn sighed, her palm on her chin as she sulked. May leaned into her chair, before an idea hit her.

"Okay, how about this: I go with the bet to see if Paul is gay or not, I give you an "I owe you one," AND, I'll help you with your chores, IF you just go on a tiny date with Conway?" Dawn thought about it for a moment, before frowning, and reluctantly nodding.

As much as she didn't want to go on a date, she also didn't want to lose to Barry.

"Deal: but it's only ONE date, and I call the shots."

"Done!" May said happily.

May wanted to thank the heavens that Dawn finally agreed! She would have jumped for joy if she wasn't in the cafeteria.

She settled for stuffing her face with her salami sandwich instead.

.

The next day, May sprinted to the library after school, looking for the right books to conduct her research.

Her face heated.

"This is actually really embarrassing. Why would the school have anything on _seduction_?" May wondered, completely flustered. She gulped, hoping no one was watching her. She kept eyeing the different books, wondering if she could find something, _anything_ that could help her.

"A history of seduction through the renaissance… Okay, not exactly what I was thinking – but might as well give it a try." She took the book, deciding to try to use this.

"What are you doing?" Drew asked, as if on cue. May jumped, a loud squeak coming out of her lips before she quickly shut her mouth.

"What are you doing here?" she whispered vehemently, flinching and feeling _way too_ _embarrassed_. She moved the book in back of her, hoping Drew didn't notice the title. Drew raised an eyebrow, wondering why she was being so secretive.

"I'm studying like I always do on this day," Drew said. "Haven't been seeing you around here lately," he noticed.

"Y-yeah, I don't need your help anymore," May said, trying to act cool about this whole situation. Drew looked amused by her words, his eyebrow raising, entertaining her words.

"Really? Finally realized you can't teach anyone algebra?" Drew smirked. May growled, her eyes boring anger.

"For your information: I actually have a better plan than doing that! Now if you'll excuse me, I have a lot of research to do!" May said smugly, before sticking her nose up and stomping away before Drew questioned her further.

.

May closed her eyes, hoping she could get some shut eye before video/photography club started. She was tired, and that book she had was so _useless._ It was simply about boring history lessons which she had no time to learn about.

Plus, she has been so busy with basketball practice lately. She has to keep in shape, especially now. She had to use muscles she didn't even know she had before. But she was pretty thankful, however. She is getting much stronger. When she flexes, she could actually see a bump of muscle now. Way better than her nonexistent muscles before training. Still, it was brutal. Ash was only going harder, making her train even more so.

It was always for her own good, he would say. He has to step it up, otherwise she wouldn't get any better. Try outs were right around the corner, he would always say.

She groaned in her sleep, snuggling into her arms even more so.

"May?" Trip questioned, wondering why she was in the computer lab so early. May yawned, rubbing her eyes.

"Hey, Trip." She waved hello. Trip sat down at his usual seat, placing his bag on his chair and turning on his computer.

"You're early," Trip observed. May nodded, smiling his way.

"Yup! I figured I might as well, you know," May said, feeling a bit nervous around Trip. He didn't seem to like her much, his words always laced with sarcasm: she wasn't sure if his personality was always in sarcasm mode.

She switched that train of thought when Serena surprisingly got there early too.

"You're early too. What a surprise," Trip said.

Serena smiled, "Yeah, I finally got here on time! The cookies I made this time were much quicker to make!" Serena explained, placing said cookies in between their desks. May smiled, leaning over and immediately grabbing some.

"This should wake me up! Thank you so much!"

Serena looked around. "Hey, where is Conway?" Trip shrugged.

"Who knows. Probably still trying to talk to the cheerleaders. Or one in particular…" Trip trailed off, rolling his eyes at his friend's antics. May scrunched her nose, but soon smiled, however. Conway will be happy to know that she was able to do the impossible... once she wins Dawn's bet anyways. Two bets she had to win... May sighed, knowing she had a lot on her plate.

"Hey, today we'll be showing a few of our videos and slideshows," Trip announced.

"Really? Awesome! I can't wait to show you guys my video for the contest!" Serena said enthusiastically. Trip nodded.

"Yeah, it's a thing we do to see each other's work and critic/ see where we can improve." The girls nodded.

"Wow, you guys will be the first to expose my million dollar idea!" May winked at the two. Serena smiled politely, and Trip inwardly rolled his eyes at her exaggeration.

"Do you two want to go get the projector from the Science and Robotics club while I go get Conway?" The girls looked at each other before smiling.

"Sure!"

.

"So, how are you liking Video/photography club?" May asked as they walked through the school halls to the science classroom. Serena smiled cheerfully.

"I'm loving it, actually. You are all so nice, I'm glad I can make more friends. Lately, some of my friends have gotten distant because they're so busy." Serena sighed, a deep frown forming. It was really only one person she was thinking about, and it broke her heart seeing how much he was struggling and didn't seem to be telling anyone about it. In fact, he's been very distant. Serena looked down to her feet. May frowned, feeling sympathetic for her friend.

"Wow, that must be hard. But hey, I'm sure they won't be busy for long. You'll always be friends I'm sure. You just need to find the time I guess." May said, hoping her advice helped. Truth be told, she never really had that problem, because she never really had many friends, Dawn being her best friend. And she was sure nothing could ever tear them apart or make them distant.

"Thanks, May. I hope so." May smiled, before looking to see that they reached the room number.

"Ah, the science room. Can't say I'm in here more than I need to be," May joked. Both giggled.

When May opened the door, Serena's eyes widened at who was there, in a white lab coat and goggles. He looked so focused, so in his element. Serena took a step back, completely taken back by this scene.

It was Gary.

Gary freaking Oak.

"G-Gary?" Serena stuttered, still flabbergasted at the sight.

Gary nearly dropped his flask at his name being called - specifically at the voice who called his name. He gulped, his eyes so scared - terrified. Serena had never seen Gary like this before. She remembered when they had chemistry together: she was unfortunate enough to be his partner, and he seemed so indifferent when in that class, she would have never guessed.

Then again, he seemed to know what he was doing too...

Still, Gary... in science club? He would openly call Clemont a nerd for participating in the science fair, she didn't think he of all people would like it so much.

"Hey... Serena... do me a favor, and don't tell anyone about this, please?" Gary said. Serena was surprised, taken back, that he seemed embarrassed. She wondered if anyone else knew besides Clemont, who is in the club as well. She was pleasantly surprised.

Maybe... Gary wasn't so bad...

Despite herself, Serena blushed.

There was more to Gary than meets the eye.

Her blush deepened, her cheeks heating.

Gary's and Serena's eyes met, for what felt like eternity, until Gary's attention, of course, went to May.

"Hey, I've never seen you before - not with Serena. You know, you're kind of cute," Gary began, smirking at May.

Serena's blush instantly subsided, sighing at Gary's antics.

Same ole, same ole.

May blushed after Gary's compliments, wondering what was up with this guy. May leaned over to Serena.

"Who's this?" she questioned.

"That's-"

"I'm _the_ Gary Oak. The top star of this school." May quirked an eyebrow.

"Top star? Wait… you're Gary Oak? Aren't you supposed to be like, into sports and not totally nerdy?" she wondered, and giggled because he completely changed his demeanor. From a very confident womanizer, to a very sheepish boy, twiddling his fingers as he tried to retort that he was _not_ a nerd, not like _those_ guys.

"Don't put me in the same category as these two fools," Gary said, a blush harbored on his cheeks. Clemont got annoyed, his eyebrow twitching.

"Hey, I resent that!" Clemont said, fixing his glasses.

Both Serena and May giggled.

.

Gary wasn't sure why, but he found himself sitting on the bleachers by the pool. He was in deep thought, wondering what he would do now that Serena knows.

Deep down, he already knew, however. He was here for the one out of two people who know about his secret of loving science (one out of three now). He was of course here for Misty. He looked over to the pool, watching the girls dive into the pool, synchronized splashes and fast movements. He already knew Misty would be one of the people ahead. She was the best after all, her body as swift as a mermaid. She was the swim team's fastest swimmer. Sure enough, Misty was the first to pop up from the water, her hands grasping for the ledge of the pool. Her coach smiled, writing down her time on a clipboard.

"Good job, Waterflower," her coach congratulated. Misty smiled gratefully.

"Thanks Coach." Misty stepped out of the pool, water dripping down her body and fiery red hair. Misty looked over to the bleachers, raising an eyebrow once noticing Gary. She went for her towel, starting to dry herself off before she decided to go to him.

"What do I owe this visit, Gary?" Misty questioned, continuing to dry her hair as she sat down next to him. Gary groaned in agony, his head hanging low. Misty frowned, wondering how serious this was. He never came to her practice unless it was something extremely important.

"She knows," Gary simply said.

"Very specific there, buddy..." Misty said sarcastically.

"Serena knows I'm in the science club," Gary elaborated.

"Ooh, how tragic," Misty couldn't help but say, not understanding what the big deal was. It's not like anything would change if she did. If anyone did, really. No one would care, in her opinion.

"No, this is bad. What if she says something to everyone else?" Gary wondered. "I told her to be quiet about it, but who knows what she will say." This was not something he wanted everyone to know. As said before, only two people know, those two people being Ash and Misty (and now Serena). Misty questioned why he was so self conscious about this, when he acts so cocky about everything else.

He really was such a dork, being scared he'd loose his reputation if the other students found out.

Misty rolls her eyes. "You know, girls actually like it when guys are smart." Gary scoffed.

"Yeah, that's why you had the biggest crush on Ashy-boy. Like he's Einstein," Gary said, sarcasm seething through his teeth. Misty blushed before telling him to shush.

"It's not like that." It was now Gary's turn to roll his eyes.

"Riiight," he said. "You and Serena are one of the only two girls that resisted my charm… besides that Dawn girl," Gary thought, his brows furrowing. It still bothered him a little bit. And all because of _Ash._ That was embarrassing enough for someone like Gary Oak.

"Maybe if you stop flirting and start treating us like friends first?" Misty suggested. "Other girls may be clueless to you, but we know you better." Gary thought for a moment.

"Nah, too easy! If I actually tried, you and Serena would be putty in my hands." This time it was Misty's turn to roll her eyes - she found herself rolling her eyes an insurmountable amount of times when it comes to talking with Gary.

"As if," Misty retorted, shaking her head. Gary placed his hands over his head, leaning against the bleachers in back.

"I don't get it. I don't get what either of you see in Ashy-boy. He barely understands girls at all," Gary muttered.

"And you do?" Misty asked, eyeing him. Gary shrugged, a smug smirk evident.

"I definitely do. Want me to show you?" Gary wiggled his eyebrows and everything. Misty laughed, rolling her eyes and crossing her arms.

"You are such a dork, Gary. Shut up," she said in between laughs. She remembered when she would hit him for that, getting annoyed with his antics and terrible jokes and pick up lines. Their friendship went beyond hating each other now though. She remembered when she couldn't stand him one bit, only putting up with him because he was good friends with Ash. But now they have been around each other enough where Misty can at least tolerate him - even call him a friend too.

"But seriously. Just to let you know, if you did give me a chance, you wouldn't regret it," Gary said, a smirk forming. Misty glared, a deep blush forming at how close he got. She still wasn't sure if he was just teasing or actually being serious.

Regardless, she couldn't let her guard down.

She pushed him aside, so she had more room.

"Please, maybe if you proved it. But we all know you just like playing around, so why bother." Misty shrugged, before standing up and beginning to head to the locker room with a satisfied smirk.

"You'll see," Gary called to her, before getting just a little frustrated that she did his signature move and just raised her arm to say goodbye, before she confidently walked into the locker room, knowing she had the upper hand this time.

He smirked at her retreating figure, always enjoying the little battle of wits.

.

May yawned, beginning to read through a magazine this time that advertised, " _10 ways to get the guy._ "

 _"Non-verbal communication, huh?"_ May thought, processing the words on the paper. " _Smiling a lot, maintaining eye contact, and pitch of voice, huh?"_ The gears in her head were already turning.

Ash raised an eyebrow.

"May? What are you reading?" May blushed, closing the magazine and hiding it in her bag.

"N-nothing!"

"Doesn't seem like nothing," Ash said, moving closer and trying to peak, being extremely curious now. May let go of her embarrassment, a smirk forming and wondering if what was said in the magazine was true. Her eyes widened, a big smile on her face and her body moving closer to him. Ash quirked an eyebrow, not really sure what she was doing.

"What are you doing?" May moved closer, but to Ash, it seemed like she was just trying to shove him away, which was obviously not her intention.

"Uhrm, nothing. Just trying to see if this thing I read worked. Apparently not." May coughed, before taking a step away. She wondered if this would really work on Paul.

But this was _Ash,_ so of course it wouldn't phase him. She paused, thinking about this situation.

Maybe she was overthinking this. She sighed, wondering if she was going crazy. May giggled to herself, however.

 _"Ash probably wouldn't know what flirting was like or what intimacy is. Although… he did say he had a girlfriend before, right?"_ May frowned, wondering if it was just that she did something wrong.

Then she shrugged.

"May, are you sure you're alright?" May jumped, before vigorously nodding, her face as red as a chili pepper.

"Y-yes, I promise!" Ash continued to raise an eyebrow, before reluctantly nodding.

"Good, we'll start with some more suicides," Ash proclaimed. May sulked, not looking forward to this at all. These were the hardest for her. She lined her feet with the baseline, before moving laterally, hoping that this will help with her conditioning. She was getting far better, and Ash was definitely impressed.

"May, you've been doing really well lately. We may have to step it up if you want to get in. But yeah, you're getting better, I'm proud of you!" Ash complemented.

"Why thank you, sensei," May said playfully before bowing. Ash chuckled at her odd antics, but really appreciated the gratitude. It made things worth it.

"Because you are doing well, we're going to have to increase your training regimen. Don't want it getting too easy for you anymore," Ash said, making May whimper.

"I thought I'd get rewarded with less work."

"Not how it works," Ash laughed. "Tryouts are-"

"Right around the corner," May finished for Ash. Ash nodded.

"Exactly."

May sighed, before plopping down on the bleachers.

"Not even a water break? 5 minutes?" May asked hopefully.

"Sure," Ash relented, before sitting down right next to her, and handing her a hand towel.

May took it without a second thought, her mind wondering how she will have enough strength to follow Paul everywhere and learn enough about him to get him to fall for her.

 _"Not how it works, I guess. I'm going to have to put in a lot more work,"_ May thought, before nodding to herself.

Ash raised an eyebrow.

"Why are you mumbling to yourself?" he asked, confused. May spasmed, before giggling, her voice an octave higher.

"No reason at all! I was just thinking aloud, don't worry about it," she explained. Ash didn't give it a second thought, instead taking a big sip of his water.

.

The next day, May eyed her target, her eyes never leaving him.

"That magazine I read was extremely helpful. I know what I have to do." May stopped to think for a moment, before a light bulb light up in her head. She placed her two index fingers and thumbs together in the shape of a rectangle, before moving them to her eye.

"It's May's expedition, and we are now looking at our primary target: Paul! He is a dark, mysterious boy, where there are a lot of questions regarding his sexual orientation. No matter what, I have to find out for myself - otherwise Dawn won't go out on a date with Conway, and then I won't have anyone to tutor Ash. I will see if Paul likes girl by flirting as much as possible, from what I read. I mean, really, who could resist a girl like me, _the_ May Maple. I'm cute, adorable, and just so lovable!" May giggled to herself, before she continued. "Anyways, it's time we get to know Paul a little more! New research mission is on!"

May casually walked by Paul, peeking into his locker, which was to no avail, because it was pretty dark in there. Her nose crinkled, before she walked past him again. This happened about 4 times before Paul eyed her quizzically.

"May I help you?" Paul finally asked, seeming a bit annoyed and eyeing her questionably. May jumped a bit, before laughing her nervousness away.

"Hi, and yes you may! My name is May Maple, I thought I should introduce myself!" May greeted before bringing her hand out to shake. She turned a bit sour, when he stared at her hand, not lifting a finger. He closed his eyes, before closing his locker.

"Paul, likewise." Didn't sound like it. "Please, can you stop hanging by my locker like that? It's weird." May blushed, embarrassed.

"I-I just wanted to get to know you, is all." May began to panic. What was something she heard: pick up lines? Oh goodness, but she only knew the most disastrous ones Dawn told her once.

At this point, however, May would have said anything, scrambling for a way to talk to him more.

"Do your feet hurt?" May blurted out.

"What?"

"Do your feet hurt… from practice, because I know some good ointment for that…" May wanted to smack herself right there. The casual line of, "Did your feet hurt… when you fell from heaven," albeit ridiculous and lame as well, would have been loads better than the lamer thing she said now… which was what was running through her mind at that instant.

"No thanks," he simply said, before slugging his backpack over his shoulder and heading to his class.

It was only until he was gone, that she got her fingers to form a camera lens once more.

"We're back with May's expedition. And it looks like this will be harder than I originally thought! Attempt No. 1: Unsuccessful!" May sulked, feeling way to dejected to try again. But still, she was never one to give up, and always one to make things much more complicated than they needed to be...

 _But that's why,_ she figured, _there was always next time!_

.

"We're back after a long day of stressful classes and hard work! But our work isn't done just yet! We have a more important mission, and that is to get Paul to fall in love with us!" May said in a anchorwomen-like voice. She took a moment to think about that. "Okay, not fall in love with us, but see if he's into girls or not. Let's go!" She ran to the gymnasium where the boys were practicing, hoping to see how Paul play and figure out what he was up too.

However, her eyes darted to see Ash already out on the court, doing some mock game with some of the other boys that were ready.

Drew was nowhere to be seen. Good, the coast was clear. She continued to follow Paul. It became more difficult, however, when Drew walked into the gym.

She wanted to cry.

Why did they make her life so complicated? She sighed, before grabbing a towel, hoping Drew wouldn't notice. She smirked, when she noticed a group of guys walking into a different room.

 _Perfect..._

She tried to converge with the crowd, hoping she can catch Paul and talk to him some more.

She sighed in relief when she made it into another room without them noticing.

However...

 _"THIS ISN'T THE GIRLS LOCKER ROOM!"_

"My eyes! My beautiful blue eyes are tainted!" May cried, running out the boy's locker room for dear life. So that's where they were going...

Dawn shook her head. Ash looked at her questioningly.

"That's what you get for trying to peek at the boys," Barry chimed in, a sly smirk on his face.

"I was not trying to peek, I swear!" May blushed, feeling embarrassed at basically being called a pervert. She was no such thing! She is innocent! Dawn merely shrugged.

Dawn was sure May had gone crazy.

"Who is this?" Barry questioned, raising a brow.

"That's my best friend, May Maple," Dawn introduced.

"Yes, I'm May, and I'm the one who will prove to you that Paul is actually - totally - into girls," May said with unfounded confidence. Barry's eye seemed to twitch at this.

"Oh, so you think _you_ can? If Dawn can't, what makes you think you can?" Both girls gave him a glare, annoyed by his remarks.

"You wait and see... Barry, was it?" Barry nodded. "I'll prove you wrong!"

"It seems to me, like we are now rivals," Barry said, his eyes burning with insurmountable determination.

"Fine by me!"

May looked around, noticing that everyone was staring right at her. A sheepish chuckle began, before she ran out.

There's always tomorrow, after all.

No reason to make even more of a full of herself today.

Besides, she needed to wash her eyes out with as much bleach as she could find.

.

Two days later, May had a whole new plan set in motion.

She was doen stalking- ahem, _observing_ him.

"Well, I guess if I can't flirt with him, I'll let my body do the talking! Body language and dress wear is key!" May said to herself, remembering the magazine mentioning non-verbal communication.

May found herself in the girl's bathroom, staring into the mirror looking down at her dress she was uncharacteristically wearing. May blushed. She had never worn such a dress. She had to borrow one of Dawn's dresses, because she didn't have something as elegant in her closet. This particular flower-pattern dress was one that was particularly snug, but tighter was good, or so the magazine said.

For May, this one wasn't all that comfortable.

Dawn was used to wearing skirts and dresses. Even short skirts.

May was not. Not like this, anyways. She was used to wearing spandex and bandannas and sneakers. Nothing as cute as this, however. As she looked at herself in the mirror, May took a deep breath in, before releasing said breath.

"Alright, I'm ready!" she declared, walking out of the bathroom, her stomach tucked in tight. She fared a cute flower dress that fit snug with black, one inch heels. She tried to look her best, knowing Paul would be very tough to impress.

As she walked closer, she noticed Barry staring at her, leaning against a locker.

Barry watched her, with a sly look in his eyes.

"Pervert," he whispered, making May's temper rise, stopping her heels against the floor.

"I'm not a pervert!" She shouted back.

"Says the girl who tried to peek at the boys in the locker room," Barry retorted. May felt appalled, her blush running all across her face.

"I-it's not like that!" she defended.

"And that's why you're of course wearing something _so scandalous._ You want to get Paul's attention, but I'm telling you now, that's not going to work. If the cheerleader's mini skirts don't effect him during practice, nothing will," Barry concluded, before walking away from her.

"We'll see about that," May muttered, her fist clenched and ready to prove him wrong.

She will definitely win this bet!

"He has to notice me like this!" May thought aloud. "It's impossible for him to _not_ notice me! Hmph, scandalous, Barry says? Well good, because I'm smoking hot right now!" Her fist clenched, ready to show Paul everything she has.

After a few days of following him, she knew exactly where he would be at that time. She had to ignore the looks, May finally being noticed after all this time. She didn't have time to care about their astonished eyes. She needed to make Paul hers! Well, _not hers,_ but for pretend of course. As her back straightened and she strode over to his locker room with confidence, her eyes targeted her person of interest.

 _"Everyone step aside while I get someone to fall in love with me,"_ May thought confidently, strolling right by his locker.

Her nose crinkled, her face turning sour when he gave not a glance to her in the hallway. _"Is this guy crazy? He might just be gay! I mean look at me!"_ May thought, looking down at her dress. She grew angry, before stomping her way to Paul again.

 _"Oh no you don't!"_

Her "dress shoes" caused her to tumble forward, right into Paul's arms.

"Oops, sorry!" Those scenes in romantic comedies, where the love interest catches the girl who stumbles over was something May thought could happen (she really hoped he wouldn't fall _too hard_ for her).

But this was far from that scenario.

"You should watch where you're going. And you should wear something that you can actually walk in, too, if you're going to keep tripping over everything," Paul simply said, before turning away.

May's fist clenched, her face turning red in anger.

"This guy… he's so unbelievable!" May shouted to the now empty hallway.

"Who's unbelievable?" May jumped at the familiar voice. When she turned around, green and blue eyes met, surprise evident.

"M-May?" Drew questioned, stunned by the way she was dressed. "What are you wearing?"

"Um… I…. Well…" She had no idea how to answer his question, especially when she was moving away, trying to get as far away as possible. He was the LAST person she wanted to see her like this.

May blushed, looking the other way and trying to cover up her - ahem - _assets._

"N-nothing!" she squealed. Drew eyed her suspiciously, completely taken back by how she looked.

"W-why are you looking so different?" Drew asked, averting his eyes. He tried to fight it, but a deep blush covered his features too.

"What, jealous?" May teased, wondering if her seducing could work on Drew too. _Oh god,_ that was _such_ a weird thought.

She stopped, deciding it would be better to practice her skills with someone else – someone _not Drew._

"N-no way! You just look weird!"

"Weird?" May scoffed, offended. She crossed her arms and stomped away.

"Wait till you have to wear a dress when I win our bet!" May smirked, her anger boiling.

She stopped, however.

"Wait a second… I have to follow Paul!" May yelled, snatching her jacket to cover herself and running after Paul as fast as she could.

.

May smirked to herself.

"My cardio is really improving! I don't think I could have ever kept up with Paul if I hadn't. And that's in these shoes, too." May, again, found herself in the bushes, looking at Paul's back, who was now at his house. She of course has been here in the past few days. She quickly stopped herself from talking, shutting her mouth with her hands as she watched Paul rummage through his keys.

 _"Now is my chance!"_ she thought, her eyes determined to get Paul to at least _look_ the other way for her. Because come on! She didn't mean to toot her own horn, but she was tooting it all the way to his house just now.

May eyed Paul, ready to make her move. She moved away from the bushes, ready to surprise him.

She froze, however, when his door opened on its own.

"Paul," an older teenager said. He looked like Paul, only his features were much warmer and easy-going compared to the stoic Paul.

"Reggie," Paul said, about to walk in, but stopped when he noticed his older brother staring out into the distance. May squealed again, completely embarrassed. The teenager looked up, and Paul turned around, his eyes widening at the girl in front of him.

"Hey, Paul, so you finally got a girlfriend?" his brother Reggie, teased, giving his little brother a wink.

Paul pinched the bridge of his nose. He didn't want it to happen, but his cheeks heated at the sheer embarrassment.

His older brother would never let him live this down.

"You followed me home?" Paul questioned – a statement, more so.

"Okay, I can explain-"

"You followed me home…" he repeated.

"Look, it's not as creepy as it seems."

"You. Followed me. Home." Paul seethed, before realizing this was exactly why he doesn't try being nice or talking to people.

He hated people.

.

May was not sure what to do anymore. In the past week, there were so many attempt to get a rise out of the boy, yet _nothing_ worked. She tried following him, trying to figure out his interest, and hoped that her impressive skills in basketball would sway him too (it was a shame, that he didn't even consider the notion, not believing that she was any good - or that she was a creep, which could also be a reasonable belief after what happened).

Every step of the way, he turned her down.

It was getting kind of ridiculous.

Nothing seemed to work.

It was only when she was all out of ideas, all out of books and magazines that could help, that she decided to see if anyone, and this is true, _anyone_ could help her.

Even the boy known for his denseness.

"Hey, Ash?" May started, getting up from the ground and wiping away dirt. It was the middle of practice, and she figured now would be a good time to ask him.

"Yeah?" he answered, Ash sitting down on the bleachers, taking a break along with May.

"Let's say you liked a girl." Ash quirked an eyebrow at this, intrigued. He wondered where this was going.

"Okay?" May frowned, wondering why it was so hard to ask for advice. She just hoped he didn't take it seriously.

"Okay, well, actually. So… what's a good way to put this? Well, my friend needs advice. Let's say a girl liked you, what would be the best way to get your attention? Or to show you that they like you?" May asked, hoping he had an answer - a better one that she could actually use.

She understood that he was completely dense, but he might have some type of solution, or can help her out in some way.

Ash thought for a moment, his eyes looking up to the sky that was a myriad of colors thanks to the setting sun.

"Well, if someone liked me, I'd want them to tell me. I think being honest with me is the best way. I'm not the best at picking up on hints, so yeah, being as straightforward as possible would help me a lot. You wouldn't believe the problems that caused," Ash laughed.

May rolled her eyes. Not like he'd tell her, anyways.

"Oh no, I definitely believe it." May sighed. She wondered if that was true. If she should just ask if Paul was gay? If he liked girls? Who knows, but she figured it was worth a shot.

"Thanks, Ash! That's actually pretty good advice." Ash nodded, shooting a brilliant smile. May smiled back.

"Why'd you ask? Do you like someone?" he wondered, his eyebrow raising.

"What? Me? _No way!_ Like I said, I was just asking for a friend," May laughed sheepishly. Ash nodded.

"Oh, okay... But you know, you can tell me, if you do..." he said, scratching the back of his head.

May smiled, thankful.

"If I ever did like anyone, I'd tell you so long as you tell me who was your girlfriend before!" May said, pointing an accusing finger at him.

"Maybe someday," Ash said, his hands up in defense. "But you know, if you need help with anything at all, I mean it. You can just ask." May stopped pointing, her hands down at their sides, processing his words. She smiled, grateful.

"Thanks, Ash. I really appreciate that."

"Now go ahead and give me five more laps!"

"And you have to go and ruin the moment…" May sighed, before sluggishly getting back on the track.

This will be a very long day.

.

May sighed, mentally preparing herself to just go up to Paul and talk to him. It was Saturday, and she planned to go to his house (hopefully he would actually answer), so she could be as honest as possible.

She did just that, walking up to his doorstep, and knocking loud.

She was surprised, when Reggie opened the door.

He was far different from Paul. Reggie seemed really friendly.

"Why, it's you again. You seem really sweet. May, right? Are you my little brother's girlfriend?" Reggie asked, a big grin across his face. May's cheeks heated, feeling a little sheepish now that she was addressing his older brother.

"Um, well no. I just... I just really needed to talk to him, actually." Reggie nodded, calling Paul down. When Paul did, he glared at Reggie. He specifically stated to _not_ open up the door for her. Reggie merely shrugged, before stepping aside and letting Paul through.

Paul was about to speak, before May placed her index finger over his lips. She glared at him, and Paul glared back. Usually, girls would cower in fear by his glares, slowly backing away, but May was different. It did shock Paul to a degree. Firstly, no one would dare touch him, let alone touch his lips like she did. Secondly, no one would ever meet his glare with their own.

He apparently never met anyone as stubborn as May.

And boy, was May stubborn.

"Okay, let's stop this game of cat and mouse, yeah? I am just going to be honest with you. So, I totally am not looking for a date or anything. But! But if I was," she started, soon stepping back and giving a small pose, one hand on her hip and another on her head, one leg curled up as she tried to give Paul the best pose she could. "Would you go for me? Do you like me?" May wondered, winking at the boy.

Paul's left eye twitched.

Paul was not amused.

Not at all.

May could tell, for it was painted all over his face. She had never seen the boy more annoyed, more aggravated, than he was. She had a knack for pushing people's buttons, but this took the cake.

"No… No, you are not my type at all. When it comes to type, your type… I don't even know what type you are, but you are _definitely_ not it."

May dropped her pose, her eyebrow twitching. _"First: ouch! He really is a blunt guy, isn't he?"_ May thought, glad she wasn't the type of girl that would cry with teenage angst when a guy rejects her. She was way too hardheaded to care about that (it's not like she really liked him or anything). But really, who wouldn't want her? Not that she cared, of course. But still… **IF** she _did_ care, she would be appalled and offended. What is his type? What does he mean by not being _his type_? What kind of type does he like? The type that are as serious and as stone-faced as him?

But again, _she didn't care._

No way did she care.

She sighed, shaking out of her stupor and drop in ego.

This was not the time for that. She remembered why she was actually here.

She eyed him suspiciously.

"So… is your type… girls?" she hesitated, wondering if he would take it okay. He was silent for a good minute, before he then let out a heavy sigh.

"Look, just because I rejected you, doesn't mean I'm not attracted to girls. You're just… _weird_ ," he explained, his hands now in his pocket and his eyes stern as he looked away from the girl.

He looked back to her, and quirked an eyebrow when May cheered.

"Really weird," he added.

"So you do like girls," May repeated.

"Simply put: yes." She jumped for joy, screaming a loud, _"Yes!"_ before running away from said boy, cheering all the way home.

Paul pinched the bridge of his nose, feeling as though he was getting a migraine.

Paul definitely did not need this in his life.

Paul sighed, hoping he wouldn't have to deal with that girl anymore, and wondering why stalker fangirls were so crazy.

.

May ran to Dawn as quickly as she could, faster than she ever thought possible. "Dawn, good news! I found out that Paul is available and not playing for the same side!" May exclaimed, rather proud of herself.

Dawn giggled sheepishly. May stopped panting, eyeing her suspiciously.

"Well, you see…" Dawn rubbed the back of her head, looking quite embarrassed.

"What?"

"Well, the thing is… I realized, he's not really my type." Dawn shrugged, making May fall to the ground.

 _"WHAT?"_

"Well yeah. He's kind of a drag, you know? He is so mysterious, but he seems kind of boring and unfriendly. I don't think we'd work all that well together anyways. Even if he did have a crush on me, I don't think I like him anyways." Dawn shrugged. May moaned, wondering if all this was for nothing. All that work she put in... nothing. May eyed Dawn expectantly.

"And you know... I don't really get why you were trying to get Paul to go out with you anyways. You could have just asked if he had a crush on me..." Dawn reminded, making May fall once again. May sat up, scratching the back of her head, before she gave a "I'm so not amused right now" look.

"You could have told me that earlier..." May sighed.

"You didn't give me the chance." Dawn shrugged. May stood up, shaking off the annoyance, now more excitement springing free.

"Either way, you still have to go on a date with Conway, okay?"

Dawn sighed. "Okay, okay, I'll keep my word!" She said this with fear in her heart, and a quiver in her tone. May didn't notice this, too happy to realize her friend's trepidation. She was far too busy cheering to say anything otherwise.

May smiled, thankful.

.

 _AN:_ Wow, longer chapter than I expected. But there was just so much going on, I had to address it all (well as much as I can). I just realized I gave a lot of emphasis to Gary and Serena too (okay, not a lot but still, there's something there maybe haha), which I'll most likely have to follow up on at some point. Haha, I think they would be funny interacting together actually. xD But yeah, hehe, I hope you guys liked it. I tried to put as many people interacting together as I could (hence why it was soooo long)! I hope you guys enjoyed! This was more supposed to be funny than anything else, but I guess there are a lot of tiny glimpses of romance sprinkled in here and there. Let me know what else you want to see. Please review, thanks!


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